


50 First Times

by Gedry



Category: Supernatural
Genre: F/F, F/M, M/M
Language: English
Status: Completed
Published: 2017-11-06
Updated: 2017-11-06
Packaged: 2019-01-30 11:39:36
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 50
Words: 27,586
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12652821
Author URL: https://archiveofourown.org/users/Gedry/pseuds/Gedry
Summary: 50 prompts related to first times.





	1. Time 1: Rome

**Author's Note:**

> 1.      Sam/Gabriel (Rome)  
> 2.      Dean/Cas: First time Castiel is sharing Dean so...(Gabriel or Sam)  
> 3.      Dean/Cas and Sam/Gabe...first time watching each other (2 pairs separate, but in the same room at the same time.)  
> 4.      Sam/Lucifer/Michael  
> 5.      Dean/Cas sex on the beach  
> 6.      Sam/Gabe something with whip cream  
> 7.      Dean/Castiel - 1st time both of them ever give a blow job.  
> 8.      Gabriel/Sam, pagan orgy  
> 9.      Sam/Gabriel. First time sharing a bed/sticking around after sex  
> 10.  Sam/Gabriel/Kali, the first time Sam joins Gabriel and Kali in bed.  
> 11.  Lucifer/Jo, the first time Lucifer's been with a woman.  
> 12.  Dean/Cas, in the Impala  
> 13.  Sam/Gabe, with Gabriel's first time having sex with someone who isn't an illusion  
> 14.  cas/sam Sam's first time with a guy but not Cas's  
> 15.  Adam/Jo, first time in public; store changing rooms  
> 16.  Dean/Cas. First time making love (as opposed to just screwing random guys)  
> 17.  Gabe, Sam, Dean and Cas are virgin Angels, trying to figure out sex together.  
> 18.  Becky/Dean. Dean starting it, just flirting and then one thing leading to another  
> 19.  Dean/Gabe, Sam letting it slip how John treated Dean growing up and Gabe reacting.  
> 20.  Sam/Dean/Castiel - first time in the new house  
> 21.  Dean/Castiel - first time sober  
> 22.  Dean/future!Cas with future!Dean watching.  
> 23.  Dean/Cas - first time Dean didn't want to leave right after and/or first time waking up with someone.  
> 24.  Sam/Castiel/Dean, their first time with Castiel's wings out.  
> 25.  Sam/Gabriel, Sam is a college freshman/sophomore still and it's his first time  
> 26.  Sam/Lucifer-First time after Jessica  
> 27.  Cas/Dean/Sam/Gabe first time coming together as a flock after the end of the war  
> 28.  Sam/Gabe first time after Gabriel is brought back to life.  
> 29.  Lucifer/Castiel, nervous  
> 30.  Dean/Castiel - The first time Castiel has to deal with an injured Dean when human in their new home.  
> 31.  Dean/Cas, tears.  
> 32.  Dean/Cas, chocolate  
> 33.  Sam/Dean, first time after John's death.  
> 34.  Dean/Gabriel, first time they make love and/or first time Gabriel lets his mask down and lets Dean see him for exactly who he is :)  
> 35.  Sam/Cas -- first time without condoms  
> 36.  Gabriel/Dean/Gabriel.  
> 37.  Sam/Gabriel - Virginity – Gabriel the older virgin neighbor.  
> 38.  Gabriel/Dean - Dean finally believes Gabriel might give a shit about him. And lets him top him  
> 39.  Dean/Cas: Anonymous hook up. Friends in a group go to a fetish club where they have a game where two people are put blind folded into a room and can't come out for one hour. They're allowed to do whatever they want as long as they remain blind folded. A challenge of a simple kiss turns into the hottest sex either of them have ever had.  
> 40.  Dean/Gabriel - Harry Potter Marathon  
> 41.  Dean/Cas or Sam/Gabe, first time getting kinky. Whips, chains, possesion (slave bracelets, bites), body friction (intentional), not being allowed to climax/having to ask for climax. Also, a little bit of cockring action would be allright, if that's okay with you, but if not, I can do w/o. :)  
> 42.  Sam/Castiel- first time in a bed/completely naked/not fast and desperate against a wall  
> 43.  Cas/Gabriel; soulbonding. Or grace bonding if you will. Bonus points if they groom each other afterwards!!  
> 44.  Sam/Lucifer wherein Lucifer has to get over his ew, humans thing because his current body keeps telling him oooo, Sam Winchester.  
> 45.  Gabriel/Kali-Gabriel's first time on earth  
> 46.  Dean/Cas, first time having sex with a new partner. After months of pining for his (seemingly straight) gorgeous blue-eyed roommate, Dean finally has Castiel all to himself.  
> 47.  Jo/Anna – first time together.  
> 48.  Gabriel/Dean- first time having sex where it WASN'T crazy, rushed, oh god it's the end of the world, sex.  
> 49.  Gabriel/Dean -- First time bondage. Dean is willing to give up control completely.  
> 50.  Cas/Dean: Dean's first time bottoming for Castiel.

“When in Rome…” Gabriel had chuckled when they flopped on the bed in their motel room overlooking the city. 

Something about doing as the Romans do or something muttered into the skin covering Sam’s throat as Gabriel’s fingers dug up under his shirt to rub over his chest before teasing at his nipples. 

After that…Sam would have done anything Gabriel wanted. 

It’s how Sam ends up in the overly large bathroom of their suite, wrapped up in a bed sheet, with part of the plant they found in the corner wrapped around his head. Sam’s feeding Gabriel grapes like a servant boy as Gabriel reclines naked in the huge tub. 

Roman bath his ass. Sam’s starting to get fed up with this little role play. But then Gabriel bypasses the grapes to suck and nibble on his fingers and Sam’s slipping to his knees next to the tub. 

It’s exactly where Gabriel seems to want him as he gets out and drops a towel on Sam’s head with a brisk order of, “Dry me, Peasant.” 

Sam grumbles, but goes with the game. His mind flashes back to their last vacation and all the crap Gabriel suffered through for Sam just dealing with Dean and the rest of his family. 

He can be the peasant boy tonight to make up for all that harassment. He loves Gabriel. Even if role-playing isn’t really something they’ve done before or that Sam has ever enjoyed. 

But there’s some merit to the experience as he gets to stroke Gabriel all over through the soft texture of the towel. Sam’s even more pleased when Gabriel slips into the bedroom and Sam figures out what the massage oil is for. 

This part of the game he enjoys. Gabriel makes all kind of noises when Sam gives him a massage at home, and here, relaxed after the bath and half bottle of wine Gabriel’s even more vocal. Sam covers his chest and arms, his legs and feet and then moans to himself when Gabriel bends over the bed and spreads his legs. 

He doesn’t have to say anything. Sam’s three fingers deep into him before Gabriel orders him to stop, directs him to oil himself up, demands to be fucked in that tone of authority that Sam is starting to think he might like to hear some more of after tonight. 

It’s not until Gabriel tells him he’s not allowed to come without Gabriel’s permission that Sam knows how fucked he really is…they both are. 

It’s like once he knows he’s not supposed to it’s all Sam can think about. His hips jerk and falter, he almost cries with the need for release while Gabriel takes everything he has to give and demands for, “More, harder, faster, don’t stop…” 

Sam thinks for a second he might die like this…then Gabriel orgasms, head thrown back and screaming without Sam even touching his dick. Gabriel collapses onto the bed shivering. Sam drops to the floor aching and burning and needing relief more than he’s ever needed it before in his life.

Sam’s not sure how long it is before Gabriel is crouching beside him. Sam’s hips jerk helplessly as Gabriel’s fingers trail along his aching dick. It can’t have been more than a minute. 

“You’re perfect,” Gabriel whispers as he tugs Sam close and kisses him almost reverently. “Such a good servant.”

Sam blushes all over. Somehow the game seems weirder now that Gabriel’s gotten off. But the sudden flash of embarrassment doesn’t stop him from snuggling closer to Gabriel’s touch. 

“Come for your master,” Gabriel orders in that voice that makes Sam think he shouldn’t disagree ever. 

So he comes. 

When he wakes up Gabriel’s smoothing the sweat off his face with a rag from the bathroom and Sam offers him a shaky smile. 

Gabriel answers him with, “I love you, Sam.”


	2. Time 2: First Time Sharing

Time 2

Watching them kiss is something beautiful, something divine. 

Castiel is a toppy, possessive bastard. He knows it, doesn’t try to hide it. 

Dean’s always been lovely in his submission. It’s not games they play, or defined roles they have. Their relationship is more encompassing than all that. 

They’re partners, lovers…friends. Castiel hangs back when they’re out in public, lets Dean use the carefully honed skills that have kept him alive for so long to get them the information they need. 

After all, Castiel is still new to humanity, naïve in many ways to how the world functions. But as confused as he is by the world, he knows exactly what Dean needs. 

So when the doors close, and it’s just them…Castiel takes over and gives Dean the relief he needs to feel whole. 

There’s only ever been one problem….Sam. 

As Castiel and Dean have grown closer, as Dean has begun to look toward him more for support and comfort than Sam, things between the siblings have grown more strained than normal, harder to bear. 

Dean’s hurt by it, but he’s too close to see what Castiel sees in Sam’s eyes when Dean leans into Castiel’s warmth and exhales in relief at the end of a hard hunt. 

Sam’s jealous, Sam’s wanting. 

Castiel’s just never been able to figure out which of them Sam wanted and then it hit him that maybe Sam needed them both. 

Castiel’s surprised when he broaches the subject that Dean’s reaction is to seize up and come on the spot…though they had been fucking for a long time that night and Castiel had been fairly close himself. 

He counts Dean’s reaction as an enthusiastic ‘Yes!’

Sam’s not given a vote, Castiel’s learned by now that the younger Winchester isn’t safe when left to mull things over. 

He goes to rent the hotel the next stop they come to and lies, saying they only have one available room. After that, it’s just a matter of locking the door and letting Dean take the lead. 

Sam’s hesitant, eyes flashing to Castiel until he leans in and claims Sam’s mouth, letting him know how much he’s wanted here too. 

After that it’s like being snuggled by two needy, giant, puppies. 

Sam fucks into Dean reverently, like he’s touching something fragile and breathless. Dean’s on his knees with Sam behind him moaning around Castiel’s dick as he sucks Castiel down. 

Castiel watching Sam with passion filled eyes. They really are a work of art, these two boys. 

“Don’t come,” Sam begs him suddenly, flushing at making the request. So vulnerable as he adds, “I want you to fuck me.” 

Castiel hears the unspoken, ‘Claim me.’

Dean must too, because he’s coming suddenly without ever being touched. 

Dean pets Sam’s hair as Castiel fucks his brother. Sam’s body a giant knot of tension until Castiel orders, “Relax.”

He knows his place with these men now. Castiel knows what he brings to the balance. 

They need a safe place, a way to connect but not have to be in control.

Castiel has a purpose, he gives it everything he has and the rewards are endless.


	3. Time 3:  First Time Watching Each Other

Time 3

Gabriel’s tight as fuck tonight. Sam can’t help the smile spreading over his face while he pushes in and out of his boyfriend’s heat. It’s good…shit, it’s always good with Gabriel. But there’s something about tonight, even though the carpet is going to leave burn marks on Sam’s knees from the friction. 

Maybe it’s the fact that while Sam has Gabriel on his knees, bent forward over the front of the couch, his brother’s leaning back against the cushions with Castiel between his knees. 

Dean’s got his hand tangled in Castiel’s hair; he’s tugging on it, directing Castiel’s movements while Castiel goes down on him. He looks good like that, Sam thinks. Mouth swollen around Dean’s dick, hair rumpled, drooling even. His back’s arching and he’s moaning like a whore while he sucks. 

Sam’s never really understood what Dean meant when his brother would close his eyes and hum to himself talking about how Castiel was in bed. 

Sam thinks he gets it now. 

Then one blue eye cracks open and Castiel’s gaze falls on Sam as he pulls off and curls his tongue around the head of Dean’s dick. 

Sam slams into Gabriel so hard his lover hisses and clenches the couch cushion in his hands. Sam’s big, some of the people he’s been with, male and female, couldn’t take him all. 

He had to work at it with Gabriel, ease into it, and nights like tonight, when Gabriel’s tense and tight around him, he needs to be careful. There’s a thin line between pleasure and pain. 

He pets at the back of Gabriel’s sweaty head while the smaller man eases back onto his dick. 

“Can’t believe you can take that thing,” Dean rumbles as he helps Castiel stand and turns him so Cas is leaning back up against Dean’s chest and sitting in his lap while Dean’s dick slides into him. Castiel’s eyes are shut; he’s biting his lip and moaning. 

“I like being full,” Gabriel answers, his voice raw as Sam reaches around to slide his hand along Gabriel’s lower belly. 

“Can you feel yourself in there, Sammy,” Dean asks as he does this slow circling grind into Castiel’s body that makes Cas whine high in the back of his throat. 

It figures Dean would be a talker. 

“Maybe,” Sam comments with shrug, palming along Gabriel’s dick casually while Gabriel bucks back into him and lets out a whispered litany of, “Please, fuck, please.” 

“I wanna see him come,” Dean pants. As Sam leans back and tugs Gabriel up so Gabriel’s almost sitting in his lap Sam watches Dean lick his lip, staring at Gabriel like he wants to touch, wants to taste. 

He’s stroking Castiel’s dick in opposing circles to the twist he’s making with his hips and Sam’s a little shocked when Castiel tenses suddenly, coming with his back arched and his mouth open but no sound coming out. 

Gabriel comes just as quickly. Sam explodes into his lover while he watches Castiel drag his fingers through his own come and bring his covered fingers to Dean’s mouth to suck. Dean smirks when he’s finished. 

“I win,” he whispers and with a few more thrusts it’s over for him too. 

Gabriel makes a noise, like maybe he wants to touch them. Dean’s eyes open with a lazy possessiveness that makes Sam think Gabriel’s not the only one to feel that way. 

Maybe next time.


	4. Time 4:  First Time

Time 4

They don’t exactly share. 

Sam’s not sure you could call it that by any stretch of the imagination. They dominate, control, jockey for position as much as he’ll let them…but they don’t give up easily and they lack the easy companionship of interested partners.

Sam’s human and as such he walks the thin line between living being to be respected and property to be owned. 

Angels are such dicks, especially the fallen ones. 

Not that Michael’s all that much better than Lucifer. He’s so high and mighty Sam’s pretty sure if you shoved a lump of coal up his ass you’d get a diamond back in two weeks. 

It’s a weird thought considering he’s talking about his own ass….technically. 

Sharing his head with these two sure hasn’t gotten any easier. But at least having them with him stops the pain of his shredded soul. Michael had agreed immediately to Death’s offer. Sam’s pretty sure it was more to get out of the cage than to really help him. But it’s not like the archangel had another choice. 

Lucifer was…harder to convince. Sam chuckles to himself as he feels the fallen one roll with pleasure in his head at the next stroke. 

Sam’s not sure who’s really touching him right now. One hand is stroking along his dick while the other shoves two fingers from the other hand into his mouth for him to suck. He knows where those fingers are going next, so he figures that has to be Lucifer even if Michael’s controlling the other hand. 

Human’s are so disgustingly nasty once you figure out orgasms. Sam had kind of thought he’d killed Michael with the first one tonight. The angel so shocked by the feel of Sam coming he hadn’t said anything for an hour. 

Lucifer had immediately wanted to do it again…and again. 

He grunts at the first press of those slick fingers against his ass. “Easy,” Sam orders. “Slow.”

He knows he doesn’t need to talk out loud but he can’t help himself really. 

The pressure eases, Lucifer has a much better respect for Sam’s body than Michael. Sam thinks it has something to do with Lucifer’s ongoing sense of ownership, his belief that Sam was made just for him. 

In any case, for an angel uneducated in the ways of sex, the guy can hit a prostate on his first try. Sam sees stars and in his head he hears a breathless chuckle. 

Then something hot flashes in his chest, there’s some kind of shuffling around he sometimes senses when the two other being inhabiting his body are moving around. Usually the warmth blossoms into horrific pain as they fight for space. 

But tonight it’s nothing but warmth and pleasure. 

“What are you doing?” Sam questions before moaning at the change of angle and the sudden synchronization of his two out of control hands. 

There’s nothing but silence in return and after a moment of bliss Sam chuckles, “You guys are making out, aren’t you?” 

No words back, but embarrassment flashes through Sam’s soul from Michael and a deep satisfaction from Lucifer. 

After that, Sam’s too distracted to think about anything other than getting off. They’re going to have to do this more often.


	5. Time 5:  Sex on the Beach

Time 5

Dean’s pretty sure he should have cut Castiel off at two, but those big blue eyes looking at him with that rarely seen hang dog face and Dean cracked. 

So now Castiel’s sucking the last of his third Sex on the Beach through the brightly colored straw that came with the glass. He’s humming contentedly as he leans heavily against Dean’s side. 

His eyes are glazed, his smile is loose, Cas is wasted. 

“You’re a good friend,” Castiel slurs as Dean drags him out into the parking lot and stuffs him in the passenger seat before strapping him in. “I’ve never been drunk before. Am I drunk? I’m drunk, right?” 

Dean’s really glad he stopped at one drink tonight. He knew Castiel was taking the break up hard but he hadn’t been prepared for it to be this bad. 

“Let’s get you home, Cas,” Dean murmurs as he gets in the driver’s seat and guides the Impala onto the road. 

It’s a silent drive until he hears Castiel start to sniffle. Dean’s whole body freezes up. He’s not ready to deal with this. Crying doesn’t fall under his best friend code book. 

“He said I cheated on him,” Castiel finally mutters. 

Dean sees red for a second he’s so pissed off. “You wouldn’t.” 

He’s totally sure about it too. Castiel’s the morally aware person in his life; he would NOT have cheated on his boyfriend. 

No matter how much Dean had privately wanted him to. 

“I never acted on it,” Castiel nods as he wipes the tears off his face. “But I wanted to.”

“Do what?” Dean gasps. He’s shocked. He thought after all these years as the wing man he knew all of Castiel’s secrets. 

“My heart wasn’t faithful,” Castiel shrugs leaning heavily back into the leather of the seat as Dean parks in his driveway. 

Dean doesn’t comment, he doesn’t know what to say; choosing instead to haul his best friend into his house and ask, “Bed or couch?”

“Bed,” Castiel whispers are he rubs his nose along Dean’s neck. “You smell good.”

“Yeah,” Dean blushes. “Okay, whatever.”

He’s flopping Castiel onto the bed and bending to undo his friend’s shoes when he hears, “Why don’t you want me?”

And oh shit, this just turned into really bad territory. 

Then Castiel’s tugging him up by his jacket and kissing him sloppily on the mouth, tasting of too sweet liquor and tears. 

“Not like this,” Dean pants as he tugs himself away. Castiel crumbles, curling into himself with a shiver. “In the morning,” Dean adds and his friend’s eyes snap back open to look at him searchingly. “When you’re sober,” Dean clarifies. “Try me again. I’m easy.”

Castiel snorts and rolls his eyes before moaning pitifully and turning a little green. “Nothing about you is easy, Dean.” But when Dean turns toward the door to go sleep on the couch Castiel calls out, “Stay with me.”

Truth be told, Dean doesn’t want to be anywhere else. Castiel’s body is a welcome weight against his as he settles down on the bed. 

A few moments later Castiel says into the darkness, “I called him your name while we were having sex. I think that’s what finished it.”

Maybe it’s how he’s standing on the edge of getting everything he ever wanted, or maybe it’s the one Sex on the Beach he shared with Castiel tonight. Dean’s not sure. But he giggles like a twelve-year-old girl and after a moment Castiel joins him.


	6. Time 6: Something with Whipped Cream

Time 6

The steady pound of Gabriel’s dick into his ass has Sam almost distracted enough to stop worrying about the mess. 

Almost…he’s a little OCD. 

But honestly, unless he keeps his eyes closed there’s nothing else for him to really look at bent over the counter like his is with Gabriel standing on a short stool behind him. 

Gabriel’s short, Sam’s tall, they improvise. 

The angle’s fucking perfect and Gabriel’s making a point to hit and miss his prostate every other thrust just to drive Sam crazy. So really, distracted as he is by the slathering of smeared whipped cream and bits of fruit all over his body and the counter top he’s eye level with, Sam’s still having a damned good time. 

Gabriel, smarmy little fucker that he is sometimes, knows it too. “God, you’re filthy,” he pants as he scratches down Sam’s back with sticky fingers before rubbing along the place where his dick is shoving in and out of Sam’s body. 

“So tight,” Gabriel murmurs as he brushes lower, slipping fingertips against Sam’s balls. They stick together, “God you’re like a giant dessert right now, all gooey and sweet. I could just eat you up.”

Sam moans, widening his legs. Moaning is pretty much all he’s capable of right now, Gabriel’s been teasing him for hours, first with bites of fruit hand fed to him between lingering kisses then a thick slice of pound cake that ended up more crumbled than not across his lap while Gabriel sucked him off after teasing Sam about needing something to wash it down with. 

Then he’d hauled out the whipped cream and Sam still can’t get the feel of Gabriel’s stubbled chin mixing with the coldness of the desert topping while he sucked bits of cake and strawberry from off of several places up and down Sam’s spine. 

Sex used to be so predictable. 

Gabriel reaches around and grabs his dick, the first touch alone is almost enough to push Sam over the edge he’s been hanging on for who-the-hell-knows-how-long. Gabriel has this thing he does with his fingertips, like he’s playing Sam’s cock like a flute. He knows it drives Sam nuts. 

“I’m going to make you come all over the cabinets,” Gabriel comments as he shoves in a little harder, squeezes down a little more. 

Sam groans, pitiful and pleading. 

“Then you’re going to lick it up,” he continues, “and when you’re done, I’m going to take you up to the shower and fuck you again.”

Sam’s brain short circuits, that has to be the reason he manages to sputter out, “What about the kitchen?” 

Who the fuck really cares about the kitchen? Clearly, years of living with his Dad and very messy brother have scarred Sam more than he realized. 

“I’ll clean it up in the morning,” Gabriel assures him breathlessly. “Just let me have this, Sam.” 

Three strokes later Sam’s screaming out his orgasm into the crumb and berry smeared countertop. Seconds after he’s done he just drops to his knees and licks up every drop of his own come off the wooden door of the pots and pans cabinet. His face is filthy, his kitchen is a mess, his whole body is sticky. 

Gabriel’s still hard, and holding out a hand toward him promising all kinds of adventures upstairs in the shower with his eyes. 

Sam leaves it a mess, whipped cream and all, and lets someone take care of him for once. 

It’s perfect.


	7. Time 7: First Time Giving a Blow Job

Time 7

He chokes on it the first time he dips his head down and tries. Dean’s hips jerk suddenly toward him and catch the back of his throat. Castiel pulls his head away and glares for a moment, Dean blushes, swipes a hand over his face, and looks away. But when Castiel inches himself forward the second time he takes note of how Dean grips the arm of the couch harder and exhales unsteadily. 

His hips don’t move. Castiel hums a little in appreciation and almost gets rewarded with being choked again. Dean’s only able to restrain himself at the last second. “Fuck, Cas,” Dean growls out roughly even as he pets at Castiel’s hair with tenderness. “You can’t do that shit.” 

He files that away for later, Castiel assumes Dean’s agitation means humming during a blow job is likely a good thing. 

Not that he’s speaking from experience. Frankly, Castiel wouldn’t know, he’s never given nor received one in his lifetime so he’s not exactly sure how this is supposed to work. 

It would have been easier if they had tried this when he was an angel. He could have kept his distance then. Dean could have done whatever he wanted and Castiel wouldn’t have had to worry about breathing, and choking, and finesse. But skill building is something he’s always enjoyed, and this new facet to his relationship with Dean is indeed a pleasurable one. Sometimes too pleasurable being that he’s distracted by how much his own erection is aching in his jeans. 

Dean tastes good, the weight of him comforting almost on Castiel’s tongue. He uses a little too much teeth on one pass, catching the hissing intake of breath as Dean’s hips back away only for Castiel to pet his hips in silent apology and shift his head to avoid more misfortune. 

He finds a rhythm that works for them, Dean’s panting turning into soft cries and his hips twitch and a sheen of sweat covers his whole body. His once petting hands are now tugging onto Castiel’s hair. He rolls his eyes up to watch Dean bite at his lower lip and toss his head back and forth. 

Then Dean’s trying to yank him away, he’s whimpering and Castiel allows himself to be tugged off only far enough to realize what’s happening a moment before the first spurt of come drenches his tongue. 

He doesn’t manage to swallow it all, it’s too much, he’s too inexperienced, but oh…it feels so good to know he’s given Dean pleasure. Dean’s fingers drag across his face shakily, gathering some off where it’s spilled off his chin. Castiel opens his mouth on a moan and sucks Dean’s fingers inside. 

His jaw hurts, he’s back is tired, he’s aching to have some relief for himself, but this connection is so good. 

Belonging. 

Dean shoves him then, unceremoniously onto his back before sliding off the couch to his knees at Castiel’s side. He drinks up the appreciative moan Dean makes when he unbuttons Castiel’s jeans and realizes how hard he is, how much he’s been leaking in his pants. 

Dean’s hands are shaking as he brushes along Castiel length; his mouth so hot as it lowers to where Castiel needs it the most. 

He cries out embarrassingly loudly in his pleasure and Dean lets go of his hip with one hand to tangle their fingers together. They do this often now, Castiel clinging to Dean as he’s overwhelmed with these physical sensations he often doesn’t understand. 

Pleasure so intense it’s almost pain and then a need for more, more, more he can’t describe. 

Castiel knows he’s squirming, Dean trying to hold him down with the weight of his body, but then he bumps something in the back of Dean’s throat causing him to spasmodically swallow and the tightness of it shoves Castiel over the edge with a roar. 

When he comes back to himself Dean is smiling at him gently, warm hand carding through his hair as Castiel curls into his touch.


	8. Time 8:  Pagan Orgy

Time 8

“So back in the day,” Gabriel murmurs into Sam’s ear while he strips him out of his shirt, “people did this stuff every weekend.” 

“Like a kegger?” Sam chuckles then drops off into moaning as Gabriel’s tongue traces along his chest to his nipple. 

“Something like that,” Gabriel nods into his stomach as he drops to his knees and works Sam out of his pants. 

“So I’m the sacrifice?” Sam questions even as he helps Gabriel get his pants off by stepping out of his shoes. 

“I love your brain,” Gabriel snickers. 

Sam wants to say he knows Gabriel loves more than that about him. But he’s distracted by the sudden warmth around his dick where his lover’s decided to suck him. 

Sam’s eyes close, then open again when he feels hands on his back, more on his thighs, something slick and smooth being slid between his cheeks as he’s nudged gently onto his back on the stone alter. There’s nothing but firelight all around him and a moving mass of people seeking pleasure in each other in any way they can. 

Drums in the background as Sam watches another man slide into Gabriel while Gabriel sucks him off. Chanting to the left of them as Gabriel’s body weight pushes Sam further back onto whatever’s sliding into him from behind. 

There’s a moment when he stiffens, a life time of safe sex instruction and too many close calls with STD’s rising to the surface for Sam to be totally at ease. Who are these people?

He looks down, seeking Gabriel gaze in the darkness, only to have his lover wink at him and flick the tip of his dick with his tongue. 

Over the course of the night Sam’s mounted by women on the alter, he services men he doesn’t recognize until he’s covered with their come. The whole time grinding himself down on that hard heat lodged inside his body, forever brushing his prostate and touching every dirty-awesome-wonderful place he never knew he had. Gabriel’s had his fair share as well, at one point draping a woman over Sam’s chest and fucking her to orgasm while Sam traded kisses with them both. 

It’s like being high, even though he knows he’s had nothing to drink. Sam’s removed from his body, watching the scene in many ways and too distracted by pleasure to really focus. He doesn’t even know where or when he is right now and with Gabriel’s trickster visage as his guide he might never figure it out. 

As dawn crests the horizon it’s Gabriel that slips him free of the plug that’s been driving him crazy all night. Gabriel who bends him over the alter and shoves his way inside in one long thrust. Gabriel whose name Sam screams out as morning comes. The ritual finished, the Gods appeased. Gabriel drags him to the ground onto soft furs with a contented and exhausted groan. When Sam turns to face him they share a smile.


	9. Time 9: Sticking Around

Time 9

He’s still panting as Sam withdraws. Gabriel slides shakily down to the cool sheets of Sam’s dorm room bed and hopes that maybe Sam will give him a few minutes before he tells Gabriel to get the hell out. 

A guy like Sam wanting more than a quick fuck from a guy like Gabriel just isn’t going to happen today, or any day for that matter. 

It’s how it goes, Gabriel’s been around. He’s mouthy, quick witted, a challenge and these jock types like him doing their homework and sucking their dicks. The occasional fuck is good too, so long as he doesn’t expect a reach around…which, come to think of it, Sam had given him. 

Weird. 

Sam walks away, heading into the bathroom and by Gabriel’s calculations he’s got about three minutes before Sam politely asks him to leave. Sam’s not the kind of guy who would toss his clothing at Gabriel and shove him out the door. But goodbye is goodbye. 

He sighs, tired in the aftermath and sore all over. Sam’s big everywhere and as gentle as he was Gabriel’s going to be feeling it tomorrow. He goes to push himself up when Sam comes back in the room and walks to the bed, sitting down on the edge of it to slide a warm, wet wash rag down Gabriel’s back and between his legs. Gabriel can’t help the moan as Sam rolls him over and wipes down his stomach too. It just feels too good, too close to caring and Gabriel’s still a little broken open and wanting from his orgasm. 

Then Sam’s shoving him closer to the wall and slipping in beside him before tugging up the sheets. Gabriel’s lost, floundering. There’s no way Sam can be ready to go again that soon. 

“So,” Sam murmurs as he settles and wraps an arm around Gabriel to tug him over and settle him against Sam’s chest. “I know we sort of did this backwards, but I was hoping you might want to go out sometime?”

“Me?” Gabriel squeaks. 

Sam’s smile is open and sleepy. He cups Gabriel’s cheek and kisses him like he’s precious, like Gabriel just shared something really personal with him. It starts to dawn on Gabriel that maybe, with Sam, he has. 

“Nobody else here.”

“Yes,” Gabriel blurts rolling toward Sam and settling himself against his larger body. This is uncharted territory, unknown country; Gabriel’s as excited as he is terrified. “I’d like that.”

“How about breakfast in the morning?” Sam questions with a teasing glint in his eyes. “I’ll pick you up, right here, at nine.”

Sam expects him to….stay. 

“I’ll be waiting,” Gabriel murmurs, more choked up than he has a right to be. 

“Good,” Sam sighs as though it’s all worked out and for tonight, maybe it is.


	10. Time 10: First Threesome

Time 10

Sleeping with your co-worker’s wife is a bad fucking idea. 

Sam knows that. Everyone should know that. 

Sleeping with your co-worker is also a bad idea. 

Sam’s pretty clear about that, too. 

But here he is, naked as the day he was born, sliding his tongue into Kali’s mouth while Gabriel kneels on the floor between them alternating between blowing Sam and burying his face between Kali’s trembling thighs. 

Sam’s pretty much holding her up now, holding her open while Gabriel works her through her orgasm. Sam’s eating up her whines and moans as he fucks her mouth with his tongue, his hips slowly sliding back and forth as Gabriel loosely jacks him off. 

As Gabriel slides away they ease her down on the mattress, she’s got this beautifully glazed look on her face, color high on her cheekbones making her glow in the lamplight. Sam turns to Gabriel, the two of them meeting in the middle between Gabriel getting to his feet and Sam kneeling down. He licks the taste of her off Gabriel’s mouth before pushing him backwards into her waiting arms and dipping lower to return the blowjob favor of a few moments ago. 

This isn’t their first time tonight. Sam can’t believe he’s still hard and Gabriel’s ass is still loose and wet from the lube of their first round. Sam plays with him while he sucks him off, listening to him pant and feeling him arch under his body. 

When he pulls off, Kali pops up to kiss him again and Sam scoops her up, out from behind Gabriel and shoves Gabriel’s thighs apart sliding her down onto Gabriel’s dick, still kissing him, before Sam licks his way down her chest to where their bodies are joined. It takes them a moment to settle, Kali riding Gabriel facing Sam, not the other way, but once he helps to steady her body on Gabriel’s lap they relax enough for Sam to help Gabriel set the rhythm of their thrusts. 

Gabriel comes with a groan, dick buried in Kali and Sam’s fingers mercilessly teasing his prostate. Sam lifts her up, turns her so she can kiss Gabriel while he fucks her from behind. It’s good, and he’s so turned on it’s stupid. 

“I’m going to fuck you next time,” Gabriel murmurs and for a second Sam’s sure he’s talking to Kali. When he opens his eyes though, Gabriel amber ones are focused solely on Sam. 

“Good,” Sam pants as he withdraws almost all the way to shove back inside her tight heat. “Looking forward to it.” 

And he is, though if someone had told him that three months ago he wouldn’t have believed them. It’s nice to know this might be a regular thing, from the noises Kali’s making and the way Gabriel’s watching him Sam’s pretty sure he could cope.


	11. Time 11: First time with a woman – continuation from kiss 4.

Time 11

He’s shaking, nerves moving through his system as he runs his hands through her hair. She hums against his mouth, a pleased noise that says she’s gotten him right where she wants him. 

Right where he belongs. 

It’s not like they haven’t messed around, after all it’s not Jo’s first time. They’ve kissed, he knows the taste of her, the way her mouth feels stretched around his dick. He knows the noises she makes when she reaches climax, enjoys taking her to the edge again and again before she finally falls over into bliss. 

But this is different, there’s nothing stopping them from finishing what they start now. 

“I love you, Mrs. Novak,” he whispers as he drags his lips across her arched neck. 

“I love you, Mr. Novak,” She chuckles before tugging on his pants in a clear indication of what she wants from him. 

His wife…so beautifully demanding. 

The dress takes forever to get off, plunging neckline and all it’s designed to be pretty, not for ease of wear. His hands are trembling just enough to make it difficult and Jo just wants to rip it. 

He knows she’s never going to wear it again, maybe never wanted to wear the thing in the first place. But bless her, his mother had insisted on a formal wedding and Jo had grit her teeth and agreed. 

His family is horrifically complicated. 

But now it’s just the two of them in their tiny apartment three blocks away from the college. He picks her up and carries her to what becomes their bedroom tonight. 

Jo’s laughing, biting at his neck until he groans and all but tosses her on the bed. Then he’s stripping out of his clothing and scrambling up beside her, cupping her breast as they kiss, sliding a hand between her thighs finding her slick and sensitive. 

He knows her body well enough by now that just the right amount of pressure on the first slide of his fingers makes her hips jerk up. She glares at him, grabs his wrists. “No,” she commands. “I want you.” 

He swears sliding into her body is like bathing in the light of heaven. She’s perfect, tight, hot, wet, and his, his, his. He had tried to imagine what it might be like, but it had never felt so good in his mind. The whole process is almost over embarrassingly quickly but he bites his lip and tries to focus, to make sure she’s fulfilled. 

He feels her tighten impossibly around his length and she cries out his name. It’s all it takes to throw him over the ledge he’s been clinging to for what seems like hours. He comes, collapsing into her warmth while his mind tries to work out what’s up and what’s down. 

She giggles, pressing kisses to his forehead while he pants. “Was it worth the waiting?” She asks. 

“You’re worth everything to me,” he answers, so in love it’s like discovering a whole new part of himself. 

She has a way of bringing out the best in him.


	12. Time 12: In the Impala

Time 12

“This is impossibly uncomfortable,” Castiel complains as he and Dean cram into the backseat of the Impala. 

“Come on,” Dean pleads with puppy dog eyes that almost rival his younger brother’s. “This is on my bucket list, Cas. It’s a must do.”

“I fail to see how sex in a car could be of so much importance,” Castiel sighs. 

“She’s not just a car,” Dean exclaims. “She’s like family.”

“I’m not sure that connotation helps your case,” Castiel huffs. “Relating intercourse in a cramped space to your family.”

“I thought we agreed not to talk about our families during sex,” Dean points out as he tugs Castiel closer by his coat. 

“Indeed,” Castiel nods. “Are we having sex right now? Because I believe we’re sitting in a cold, dark vehicle while you try and convince me that this is a good idea.”

“You want me to warm you up?” Dean comments with a grin. Castiel can’t help himself, he chuckles. Dean is far too cute for his own good. 

“If you insist,” Castiel huffs but then he’s straddling Dean’s lap while he bangs his head on the ceiling. 

“Easy,” Dean murmurs, reaching up to ruffle his hair before unbuttoning his shirt and leaning forward to attach himself to Castiel’s nipple with a pleased groan that Castiel mimics. 

He struggles out of his shirt and coat before tugging Dean back far enough to pull Dean’s shirt off over his head. They kiss leisurely, fingers tangling together in a give away of how much they mean to each other even though it goes unsaid. 

Dean unbuttons Castiel’s pants and he falls over trying to wriggle out of them without having to get off of Dean’s lap. They laugh something silly and funny overriding everything in Castiel’s upbringing that’s screaming how men in their thirties do not make out in the back of car on the side of the road where they could easily be arrested. 

Dean bending over to lick around the head of his erection pretty much shuts up the whole voice-of-reason thing Castiel had going anyway. They try every angle they can think of, but reality is cruel mistress. 

Dean is a big guy and Castiel’s not exactly small either. If they concentrate they’re able to gain penetration but then neither of them can move without it slipping back out, and they can’t get their hips together without someone hitting their head or risking putting out a window. After a half hour of struggling they settle for mutual masturbation in the backseat culminating in them fighting about Dean using Castiel’s coat to clean up the upholstery. 

“It’s my favorite coat!” Castiel exclaims, all indications of post coital bliss dissipating in the heat of the moment. 

“We can’t just leave her like this,” Dean argues. 

“You should plan better,” Castiel snaps, yanking his coat away and groaning at the smears already all over it. “Gross, I hate this car.” 

“Yeah,” Dean mutters. “Well, she hates you, too.”

Silence, then Castiel tries to smother his laughter in his ruined coat while Dean glares at him from the other side of the back seat. A moment later his lover joins in and they scoot over to snuggle and laugh at their own stupidity. 

“I’m never doing this again,” Castiel says with a smile. 

“I know,” Dean snorts. “Let’s get some dinner, I’m hungry.”


	13. Time 13:   Gabriel’s first time having sex with someone not an illusion.

Time 13

“Why are you looking at me like that?” Sam asks.

Gabriel’s eyes snap up to his lover’s face immediately. “Like how?”

“Like you’re going to vomit,” Sam comments as he crosses his arms over his bare chest. “It’s not exactly flattering.”

“I’m nervous,” Gabriel blurts then shames himself even more by blushing and the hand he lifts to wipe across his forehead is trembling. This is officially now more humiliating that being killed by your little snob of an angelic brother. In fact, it’s even more embarrassing than being brought back to life by Bobby Singer. 

Gabriel’s just going to run away to his hotel room and die right now.

He steps backwards, flustered, looking for his shirt, his shoes. He needs to find the door and exit pronto, before Sam starts laughing at him. 

But then Sam is cupping his cheek in one gigantic hand and everything inside Gabriel sort of rolls over like his very soul is exposing his belly to this human. Sam’s crowding his space in seconds, bending down and making Gabriel drunk off his kisses before he can argue. Long moments pass as his brain is boiled down to simple thoughts of warm, safe, good. Gabriel’s unable to stop himself from whispering, “I’ve never done this before,” when their lips part. 

Sam laughs in his face even as he’s tugging open the buttons on Gabriel’s jeans and sliding the zipper down. “Liar.”

“I made them all up,” Gabriel admits in a rush because shit Sam’s tugging his jeans down and murmuring approval at Gabriel’s lack of underwear. His rough hands are gripping his bare hip and circling around Gabriel’s erection, rubbing the fluid leaking from the tip around with his thumb. “The others, they weren’t real. I’ve slept with gods and puppets, but never a human. What if I can’t make it good for you? What if I hurt you? What if we don’t fit together?”

He’s rambling, gasping as Sam strokes him smooth and long at a pace so slow and steady Gabriel’s hips want to jerk up for more. Sam’s other hand is sliding up his stomach and across his chest to rub across his left nipple. Gabriel groans as his head falls back at the how good it feels. 

“You’re nipples are sensitive,” Sam comments like Gabriel hasn’t just poured his vulnerability out all over the floor between them. 

“What the hell does that have to do with my erotic neurosis?” Gabriel snaps. It’s like Sam’s not even listening.

“Mine are too,” Sam answers with a pointed look down at his own chest. 

“Oh,” Gabriel breathes dumbly, and then, as understanding dawns, “Ohhh.”

He lifts a hand from where he was certainly not clinging to Sam’s sides to rub his thumb back and forth over Sam’s right nipple making him moan. Some instinct Gabriel didn’t know he really had making him lean forward and lick it before closing his mouth around it and rolling it between his teeth gently. Sam moans, “You are the perfect height, you know that right?” 

Gabriel smirks against his chest and spreads his legs a little further apart when Sam reaches for the lube. 

He’s unzipping Sam’s jeans and sliding his boxers down with them when Sam works one lube-cooled finger inside of him for the first time. He hits a place inside of Gabriel that reminds him of flying and he pants, “I have to sit down,” after a few slow strokes. 

He straddling Sam’s lap in the hotel chair in the corner, filled to the point of bliss by Sam’s dick and crying out his pleasure into Sam’s neck. His wordless joy is a direct counterpoint to Sam’s litany of, “Perfect, Baby. You’re so damned perfect.” 

Sam grips him hard and pours inside of him, Gabriel gasps at the wet heat inside. It only takes a few shaky strokes of Sam’s hand along his length for Gabriel to come too. 

Afterwards, Sam holds him close, like he’s precious, like this means something, like Gabriel’s special to him, and Gabriel hopes he’s right.


	14. Time 14:  Sams first time with a man but not Castiels.

Time 14

He’s different than he used to be, back when he was an angel and Sam was an abomination. 

Castiel’s human now and after two years on his own he’s rounded out as a person, personality and all. Working with him these past few months has been a welcome distraction. 

Not that Sam is happy Bobby got hurt, but he and Dean have been driving each other nuts for a while and getting a break is awesome. Dean stays home with Bobby and Sam gets to keep hunting with the only guy Dean trusts to watch his little brother’s back. 

Of course, Sam’s not sure Dean is really aware of how much of Sam’s backside Cas is watching. 

So yeah, he’s checking Sam out, he’s noticed. Sam hasn’t called him on it directly but when he gets caught Cas’ face has that same impassive defiance he had when staring down an archangel. He wants Sam; he doesn’t care if Sam knows it. 

So when Sam slides into his personal space one night as Cas is getting out of the bathroom still damp from a shower he figures his friend isn’t really surprised. Still though, kissing is one thing, Sam loves to kiss. But fucking is another and Sam hasn’t exactly gone all the way with another guy before. 

Cas’ intensions are clear from the beginning, Sam’s on the bed and naked pretty quickly even if the whole thing is kind of a blur of body heat and sinful tongue in all the right places. His legs spread willingly, just because he’s new to this dance doesn’t mean he doesn’t want it, but Sam flinches at the first press of Cas’ fingers against his too tight opening. 

“Sam?” Castiel questions.

“I’ve never done this,” Sam admits, rolling over onto his stomach so he can bury his red face in the sheets. 

“Ah,” Castiel comments like he’s digesting that little bit of info. Sam’s expecting him to want to talk about it, but then…talking never has been one of Castiel’s strong points. 

He breathes out to relax as Cas pushes his legs apart and slips between them, using his hand to keep Sam in position on the bed until Sam settles, exhales, relaxes. Soothing strokes of Cas’ hands up and down his sides in long sweeping motions that slowly work their way to his center before holding his cheeks apart. 

Castiel’s tongue…there, where almost no one has ever touched him. Sam’s shaking with a mixture of passion, embarrassment, and nerves at first. But sometime between Cas’ first sweeping licks to when he points his tongue and works it all the way inside Sam forgets everything but how good this feels, how much he wants more. 

He’s begging, he’s sure of it, and he doesn’t honestly care. 

A finger joins the tongue in his ass before Castiel slips his mouth away to bite into Sam’s back just hard enough for him to feel teeth again and again as one finger turns into two, then three as Sam scrambles to get on his knees.

Cas slides inside to the hilt in one long stroke. Sam whimpers when he bottoms out, tries to jerk away, something skittish inside him that Castiel soothes with a grip on his long hair and, “Shh…I’ve got you. I can lead you through this, let me,” whispered into his spine.

Sam gives him everything and comes screaming with Castiel’s hand wrapped around his dick just moments before Castiel explodes inside of his body. 

They collapse on the bed touching each other gently in the aftermath when Cas suddenly chuckles. 

“What?” Sam breathes. 

“This was fun,” Cas smiles, looking less world weary than Sam ever recalls seeing him before. “I enjoy teaching you new things. We need to do this more often.” 

Sam shoves him off the bed laughing.


	15. Time 15:  First time in public – store changing room.

Time 15

The lock’s broken to the tiny stall so in reality it’s just Jo’s foot holding the door shut. Something about the idea of there not even being a lock to keep the world out adds to the excitement. 

Not that she needs to be any more excited, she’s already a few breaths away from her second orgasm as it is. Adam really knows what he’s doing. 

They don’t get to see each other much, not since he started med school. So this shopping excursion quickly turned into mindless flirting and culminated with Jo leading him into the tiny row of stalls in the women’s dressing room to show off a lacy little bit of nothing she had no intension of actually buying. 

She’s pretty sure they’ve ripped it by now, it’s still hanging over her left shoulder but the neck on it feels way too big. If they finish before they get arrested she’s just going to have to pray it’s not stained or they’re going to have to buy it and she’s not going to be able to look the sales person in the eye. 

It was supposed to be a tease, a game, backfiring on her when Adam reached out to cup her breasts, rubbing over her nipples before dropping to his knees to nudge her thighs apart and lick her through and around the scrap of material some designer decided to call a thong. 

It’s like a shoe string with a napkin attached. 

The way he’s holding her pressed up against the side of the stall with her leg closest to the door slung over his forearm and her other curled around his thigh makes a nice view in the full length mirror while he fucks her. Jo’s distracted from her door holding duties by the bounce of her own breast and the sweat dampening Adam’s back. 

Her foot slips; the door swings in and bumps them both. 

“You want it open?” Adam breathes out against her skin. “Want me to carry you out of here and fuck you out in the open?”

Jesus, where did he get such a dirty mouth? 

“I’d like that,” Adam continues like he can’t here her muffled whimpers against the back of her own hand. “Like for everyone to see how good I fill you up. How wet you are for me. I think you should come now, Baby, unless you want someone to come in here and watch us.”

She bites his shoulder to keep from screaming as his fingers reach between them and give her the friction she needs to push her over the edge. Jo’s distantly aware of him groaning into her neck as he comes. 

He slides her down until her feet touch the floor and smooth the hair back from her face with a tired smile. 

“You totally have to buy this outfit,” Adam comments as he plucks at the strings that used to hold it shut. 

“You buy it,” Jo snorts as she reaches shaky hands for her jeans. “You ripped it.”

She’s a little surprised when he does just that, even having the nerve to wink at the sales lady when she gives him an odd look. He’s grinning like a lunatic as he heads back over to where she’s absolutely not hiding near the door and says, “I’m hungry. How about lunch and then we go home and you put this back on?” 

She blushes all the way through drinking the milkshake he buys her.


	16. Time 16:  First time making love instead of just sex.

Time 16

Dean’s used to the rustle of clothing as he yanks it off or tugs it down just far enough to force it out of the way. He’s used to the rough handling from men he doesn’t really care about or know that well. He’s experienced in picking himself up, cleaning himself off, and letting himself out when it’s over. It’s what he’s done all of his life, flings, one night stands, maybe a week here or there. Nothing serious, nothing worth settling down with. 

Nothing like this.

Cas kisses him with a singular focus Dean’s only seen him use before on the machines he restores. All that attention turned toward making him feel wanted, making him feel…loved. 

He still stumbles over the word, but he’s making progress. 

Castiel’s hands undo his belt, tug it through the loops until it’s free and toss it to the side and out of sight. Callused hands able to do such intricate work during restorations tremble and stumble through Cas unbuttoning Dean’s jeans. But he doesn’t pull them down or reach inside and there’s something so sweet in the knowledge that it’s not just Dean’s dick that Cas wants, it’s all of him. 

He’s stripping away the tie and struggling through the buttons on the white dress shirt while Cas slides his flannel off and digs up under Dean’s t-shirt with the intent of tugging it over Dean’s head. He steps back long enough to yank it off while Cas tugs his shirt free and folds it sloppily before tossing over the back of the nearby chair. Dean goes about yanking his boots off as attractively as someone can do such a thing before sliding off his jeans and his boxers and leaving himself naked, hoping Castiel approves. 

It’s funny, he’s never been insecure about how he looks before. 

“Beautiful,” Cas breathes. But when he reaches out to touch, it’s Dean’s cheek he cups while their eyes meet. Dean blushes, it’s not just his body Castiel is talking about right now. 

Dean drops to his knees and reaches for Cas’ pants, working them over narrow hips before remembering his shoes and tugging them off as well. Tiny kisses pressed reverently to his lover’s thigh before Dean turns his attention to Cas’ erection. Tasting him for the first time better than Dean’s been imagining it would be during the time they’ve been dating. The noises Cas makes while Dean first licks then sucks him so slowly are wonderful and Dean wants more of them. But the hand carding lovingly through his hair tugs him off with a groan and Cas slumps down on the edge of the bed pulling Dean between his legs and kissing him passionately, like it’s all he’s been thinking about. 

“It’s been a very long time since I’ve done this,” Cas whispers when their lips part. 

“I don’t think I’ve ever done this,” Dean blurts then blushes before adding, “I mean I’ve had sex, but I’ve never…”

“Made love?” Cas offers with a gentle smile. 

“Yeah,” Dean nods before nudging Cas further back on the bed and crawling up beside him. Their legs tangle, their arms do the same, Dean kisses him over and over while their hands wander over each others bodies seeking out hidden places that give pleasure and Cas rocks his hips in a slow but perfect rhythm against Deans. 

Making love, it’s new but totally not unpleasant. He and Cas spend most of the night learning each other and holding off their orgasms as long as they can so the moment doesn’t end. Then Dean cleans them up and Cas tucks them in close together in the early light of dawn. They sleep. 

Then rinse and repeat in the morning.


	17. Time 17:  Virgin angels trying to figure out sex together.

Time 17

“I think the kissing would be…nice,” Sam comments hesitantly as they spy on a pair of humans without their knowledge. 

“You would,” Dean snorts before nudging Sam jokingly with his wing. 

They’re crowded together, pressed in close so they can get a good view of what’s happening on the bed. Castiel’s not certain how they ended up in this particular place with this couple, but the four of them had been debating for a very long time both the mechanics, and the enjoyment of physical pleasure. 

As of yet they haven’t come to any conclusions. Gabriel and Dean have a nasty habit of just taking the opposing opinions so they can continue to bicker. Sam is always curious, and Castiel has to admit he’s interested in the possibilities the act of making love would open for him. 

Sometimes, when his wings are being groomed, he wants more. Not that he’s really certain what ‘more’ might be. So when Gabriel raised the stakes of the ensuing argument with a commanding, “Let go watch it then, if you’re so damned sure it’s gross.” He had been the first one to take wing. 

The two men on the bed are naked now, one gripping the others hair and pressing his chest into his mouth while he moans. “Nipples,” Gabriel mutters distractedly. “Who would have thought they could feel so good.” 

“Maybe,” Dean murmurs. He still sounds as though he thinks this is all a terrible idea, but when Castiel turns toward him his feathers are puffing up and his wings are trembling. 

The men are moving now, one on his knees while the other kisses down his spine before touching that hidden place between his cheeks with his mouth. “Okay,” Dean blurts loudly. “There is no way I’m doing that.” 

The licking gives way to fingers, then to more somewhat sticky liquid being applied to the man’s erection before he grabs the other’s hips and steadily inserts his penis inside. 

“Oh,” Sam breathes out slowly, his wings drops until they trail the ground. Gabriel might have made a sound like a whimper to his left but all Castiel is really aware of is Dean grumbling, “Who would possibly want that?”

“I do,” Castiel snaps having had all he can take of Dean’s attitude. “I want it, I want to be touched and caressed. I want to give and receive pleasure in this way. I want more than what I’ve had thus far. The grooming, it’s not enough for me. I want claiming, mating, I want….I just want…”

He can feel his grace throbbing; his wings are flaring up and out and tense as though he’s ready to fly. Dean grabs him, tugs him close to his body and Castiel can feel in his grace the thrum of arousal, a matching counterpoint to his own. “Don’t go.” Dean orders as his puffed up wings slam shut around Castiel and hold him close. It’s all the permission he needs before lunging forward and slamming his mouth against Dean’s so hard their teeth bang together. Dean steadies him, gentles him and Castiel melts into his arms. 

A few moments later Castiel gasps as Gabriel’s hands fumble through Dean’s quivering wings to stroke Castiel’s sensitive wing joints. Dean groans loudly as Sam’s long arms slide under his wings to palm at him erection. 

He groans so loudly, in fact, that the humans on the bed stop their frantic movements toward climax to look in their direction. The veil between them slipping as the angels become distracted by these new sensations. 

“We should take this some place more private,” Sam says conversationally before licking Dean’s ear. 

Castiel thinks of their nest and closes his eyes, knowing his new lovers will sense his path and follow.


	18. Time 18:  Dean starting it, just flirting and then one thing leading to another.

Time 18

It wasn’t a joke…not really. 

Dean’s just a little bit competitive and he’s grown accustom to things being a certain way between he and his brother. Dean’s the hot one, Sam’s the sweet one. It’s how it is, how it’s supposed to be; one of those life centering things that gives you security when nothing else makes sense. 

Then there’s Becky, not only does she prefer Sam, she goes bat-chit crazy over him. And if that weren’t bad enough, she takes one look at Dean and seems…disappointed, like he’s not at all as good as she expected him to be. 

It rubs him the wrong way. So wrong, it turns into an obsession. 

He just wants her to get how things are supposed to go. 

He slips her a few emails at first. What? Dean can use a smart phone as well as the next guy. He just acts like he hates technology. He says couple because she sort of never answered the first two. 

Once she does though, well…next thing you know, Sam goes out for pizza and Dean’s calling Becky. Underneath all the crazy…she’s actually really nice. 

Dean’s not used to nice. He’s not used to someone who cares. After all, Becky might like Sam better, but that doesn’t mean she doesn’t care a whole lot about Dean too. She read the books; she knows how it all went down. 

The next time they come through close to where she lives Sam goes out on stake out on his own and Dean meets Becky for a very late dinner, or a very early breakfast, depending on how you look at it. She’s direct, a little loud, and too personal for him to be really comfortable. 

But she flirts right back when he shoots her a line and holds her own all the way back to the hotel room. Sam’s out for the rest of the night and Dean’s pressing every chance he can get to win this one. 

Instead, he ends up sleeping, fully clothed, with her curled up against his chest. It’s…really nice. When Sam wakes him up in the morning with a grunt and a kick to his foot Becky’s long gone. 

It takes Dean two weeks to figure out he feels pretty shitty about getting ditched like that. 

She drives him crazy over the next few months, culminating in phone sex so hot he thinks it melts his cell. The next time they get anywhere near her state Dean ditches Sam like a cheap date and drives straight through to her apartment. 

The night’s nothing but a haze of thrown off clothing and kisses, smooth skin and his heart pounding in his ears. It’s not until he’s pressing her down and sliding all the way deep inside her that Becky’s face cracks into a huge grin followed by a gasped out chuckle. 

“What’s so funny?” Dean asks as he slides back just to thrust in again. Fuck, she’s tight. 

“I knew the only way to get you was to act like I liked Sam better,” Becky rolls his nipples between her fingers like she read it in a book somewhere that it drives Dean nuts. 

Maybe she did. Weird. 

“You just couldn’t stand it, could you?” She whispers as she wraps her thighs around him and holds him tight as he jerks his hips and pushes them both closer to orgasm. 

“Are you shitting me?” He pants. 

“If I had gone right to you,” Becky’s words broken off by a groan. “You would have had sex with me and forgotten all about me. This way it’s different, right?”

He hears the uncertainty in her question. “Yeah,” he assures her. “It’s different.” 

She comes then, tugging him over the edge with her. When he’s panting beside her he huffs and nips at her shoulder with his teeth. “You played me.” 

“Sure did,” Becky smiles. 

Dean smiles back. Either way, he’s still a winner.


	19. Time 19:  Sam letting it slip how John treated Dean growing up and Gabe reacting.

Time 19

Gabriel exhales slowly, praying silently to who-knows-what for strength as Dean stomps off down the hallway to his room. 

Hell, Gabriel’s not really even sure what set him off this time, could have been anything. 

Dean’s not an easy guy to get to know and Gabriel’s ready to pack it in. 

It’s pretty obvious Dean doesn’t want him here, not really. 

“Has Dean ever told you about our Dad?” Sam says casually from behind his laptop screen like he hasn’t just witnessed what is most likely the death toll of Gabriel and Dean’s short lived relationship. 

“No.”

“Hmm,” Sam leans back and Gabriel notes the laptop closing with a clicking noise. It’s strange, Sam’s got a double major, he’s always studying. “He treated Dean like a forty year old in a ten year olds body. Dean raised me, Gabriel. He fed me, read to me, checked my homework. He looked out for me at school and took the hits for me at home. Our father…he’s not so nice sometimes. My whole life he was always telling Dean how he wasn’t good enough or smart enough, that he never did anything right. It was rough.” 

Rough doesn’t begin to cover it; Gabriel can see it hovering just behind Sam’s eyes. There’s more to it than what Sam’s telling him. “What does that have to do with now?” 

Sam’s eyes shift toward the hallway, like he’s looking for Dean to be hovering around the corner and bust out to smack them both any second. “Gabriel…he shoves you away because he wants you to stay.”

“That makes no sense, Sam.” 

“I know,” Sam rolls his eyes. “But it’s what he does. Dean’s spent his whole life thinking he didn’t deserve anything good, that he wasn’t worthy of being happy. You scare him Gabriel, you make him happy and he’s…”

“Sacred I’ll leave him, so it’s easier if he makes me go first.” 

“Something like that, yeah. But he’s already going to kick my ass for telling you this much so I’m shutting up now.” Sam turns back to his work. Gabriel hovers for just a minute, before turning and making the trip down the hallway where he opens the bedroom door and finds Dean curled on the bed facing the wall. 

“Leave me alone, Sam.” Dean voices sounds choked like he’s been crying. 

“Sam’s studying,” Gabriel murmurs, sliding into the bed beside Dean and curling around him tightly. “and I’m not leaving you alone.”

Dean mutters, “I’m going to fucking kill Sam.” But he reaches back and tugs Gabriel’s arm a little tighter around him, snuggling back into the embrace. 

Gabriel smiles, pressing a kiss to the back of Dean’s neck before whispering, “Your room’s nice, never been in here before. How about you let me stay a while?” 

“How long?” 

“Forever.” Gabriel assures Dean, holding him even tighter.


	20. Time 20:   first time in the new house.

Time 20

Sam chuckles as he watches Dean scrape the last bits of popcorn ceiling down out of the living room. Who would have thought his older brother would have such an aversion to that kind of décor? He hears huff slightly to his left and turns. The man, because Castiel is just a man now, has become twisted up in Sam’s head as his other brother, a member of the family. 

Cas is prying staples out of the hardwood floor they found under shag carpet in the dining room. Who would have ever thought they would have a dining room? 

The house is trashed, abandoned for years and infested with every horrible animal thing a person could think of. Sam’s been digging dead rats and squirrels out of the attic for weeks now, every time they get a whiff of a funky smell. He shivers at the memory of some of the crap he’s stumbled upon before turning his attention back to Dean, now standing right up next to him. Personal space is a concept Castiel has never understood and Dean and Sam forgot about a long time ago. 

“I zoned out, didn’t I?” Sam asks at the odd look on his brother’s face. Dean shrugs before nodding, white powder dusty fingertips reaching out to brush along Sam’s jaw. It’s something that’s been happening since the wall came down. “How long?” 

“Only about twenty minutes,” Dean dips his head closer, lips brushing along Sam’s tentatively, like Dean’s still not sure this isn’t all just going to fracture in his hands. Sam bites his lower lip before letting Dean back away. He watches as his brother’s eyes open wider before narrowing with intent. 

Dean’s hot, Sam’s allowed to admit that now. 

“Come on,” Dean nudges him toward the steps leading to the bedrooms upstairs. “Cas has his panties in a bunch about us trying out the new shower or some shit.” 

Yes, the master bathroom. The room in the house Castiel snared as his project. He’s spent weeks in there ripping shit apart and reading books on installation. Dean and Sam have been barred entry at every turn until it’s finished. 

They stumble through the door to find the third member of their family lighting candles in the nude. 

Sam’s dick gets hard so fast it actually hurts. Dean stops breathing. Sam doesn’t blame him, even with the scars that now cover so much of Castiel’s frame, he’s beautiful. 

“Shower?” He asks gruffly. 

Sam’s not even going to talk about how fast he and Dean get naked and stumble through the door of this thing that Cas calls a shower. “You made us a shower big enough for all of us.” Dean comments as the spray comes from all directions. 

“I find it relaxing,” Cas answers with that half a smile Sam’s starting to love. “I thought it might also be convenient should we begin hunting again.” 

The way he trails his hands down to stroke their dicks makes Sam think Cas is full of shit. “You have a kink for shower sex.” He accuses. All his guesses answered when Castiel blushes bright red. 

“I don’t get why the bench is so high,” Dean mumbles as he looks around. “Why are the towel bars in such weird places?”

“Those aren’t towel bars,” Castiel chuckles before dipping Dean’s face back and kissing him roughly, just like Dean likes it. “And the bench is high because Sam’s so tall.” 

“Handles,” Sam whispers as he reaches up to grab one as Cas pushes Dean to his knees and guides his mouth over onto Sam’s leaking cock. It only registers long enough for Sam to admit it’s good he has something to hold onto before Cas is fingering him open and Sam’s not thinking about anything anymore.


	21. Time 21:  first time sober, follow up to Kiss 49.

Time 21

Castiel avoids Dean like he has the plague for two weeks after what he has come to think of as “The incident.” It saddens him to realize that Dean seems less than concerned by Castiel sudden absence, in fact there a few nights where Dean walks right past him in the living room to head directly down the hall and slam his door behind him. 

Castiel starts looking for other living arrangements. 

But then, on a random Friday night, Dean comes home from working and says, “I’m hungry. How about some pizza?” 

Castiel hesitates, but everything inside him just wants to be with Dean, so as shamed as he is by his fickle emotions he agrees and finds himself rushing down the sidewalk at Dean’s side to what it turns out happens to be his favorite pizza place. 

“You don’t like it here,” he comments as Dean holds the door open for him. But Dean only shrugs. 

“It’s growing on me.” 

They’re seated when the waitress asks for their drink orders. Castiel has a flashback or a few weeks ago. A memory of Dean ordering one too many beers and then the feeling of being held in his arms, Dean’s hot mouth working his open, his rough hands up under Castiel’s shirt while he whispers brokenly about how much Castiel means to him, how much Dean wants him. It hurts, it hurts so much Castiel almost launches up from the table and flees. But then Dean asks for a soda and orders Castiel’s favorite pizza even though Dean hates pineapple. 

Castiel is so confused. 

They talk, really talk, about Dean’s strained relationship with his father and younger brother, about how Castiel hasn’t gone home in a very long time, so long that he is uncertain of his welcome now. Dean picks all the pineapple off his side of the pizza with a fork and feeds it to Castiel carefully between slices. If this is a dream he doesn’t want to wake up. 

Dean pays, even though Castiel argues. Both their budgets are tight. The walk home is comfortable, slowly paced, with them walking so close together in the cool fall air that their arms brush again and again. 

For the first time in two weeks Castiel thinks maybe they will be able to salvage their friendship. Though it’s not what he really wants from Dean it’s still something precious. 

“Cas,” Dean murmurs as they shut the door behind them once they enter their apartment. “Can you do me a favor?”

“Of course,” Castiel answers without thinking. Dean almost never asks him for anything. 

“I want you to pretend.” Dean says so seriously that it doesn’t even occur to Castiel how close together they’re standing with Dean advancing on him slowly. 

“Pretend what?” He’s so confused. 

“That this is the first time…please.” 

Dean’s so close Castiel can see the golden flecks in his eyes and could count the freckles splattered across his nose if he really wanted to. He nods, to mesmerized to voice consent. It’s enough for Dean. His friend leans forward and claims his mouth passionately, with as much longing as Castiel has long felt in his chest. 

“You were drunk,” he accuses as Dean pulls back just enough to nuzzle his cheek. 

“I know,” Dean sighs. “I was a drunk asshole, but if you want I could be your drunk asshole.” 

“You’ve always been my drunk asshole,” Castiel huffs before kissing Dean again, and again, and again, all the way down the hall to his room.


	22. Time 22:  Dean/future!Cas with future!Dean watching.

Time 22

He doesn’t remember being so young, or so tender. The way his younger self touches Castiel, like he’s something to be savored, protected, loved even. 

Dean doesn’t remember how to love anymore. Life has beaten that ability out of him bit by bit. 

Cas is moaning, almost whimpers as his fingers tremble and his body quakes. Dean’s not sure if it’s the pleasure, or nerves, or the start to withdrawals because Cas had demanded being sober for this one experience; like he plans to burn it into his brain for always. 

Maybe he does, Dean’s pretty sure this is something he’s never going to forget. The play of the moonlight as the other version of him slides down the bed to give Cas head. He can’t fathom ever allowing himself to be so vulnerable. Cas’ hands hovering in the air around his head before he cries out and buries them in the other Dean’s short hair. He watches his oldest friend’s hips jerk and twist as he tries not to thrust. There’s a shadow in the back of his mind, something like sense memory maybe. He can almost feel how full the other Dean’s mouth must be right now. 

He’s shocked when Cas throws back his head and comes in Dean’s mouth. The hungry noises his younger self makes, like it’s something he always wanted. He hears Cas make a noise like a dry sob as Dean turns his now pliant body over and parts his cheeks to bury his face against the opening to Cas’ body. It takes him a minute, but just as Cas exclaims, “Oh fuck!” He gets it. 

He’s using Cas’ come to lube him, working him open with his tongue and slicking the passage with come. No lube here, a luxury they can’t afford. The kid’s smart, Dean has to give himself a little credit. He manages to hold out until Cas is pleading, breathless urgings into dirty sheets. Then Dean’s lining up and sliding in, working his dick past the resistance until his hips hit Cas’ ass. It’s a thing of beauty really, watching the purer version of himself finally give something to his best friend that Dean himself can’t offer. 

If the world were fair, he’d be joining them. But it’s been over a year since Dean’s been able to get it up, not even able to allow himself that much of a release anymore. 

If the world were fair, then tomorrow would never come. But it’s not and dawn’s already breaking over the tops of the trees through the window. 

He watches his younger self pull out, roll Cas over and enter him again. Sweet kisses, full of promises that will never see the light of day shared between the two before Castiel comes again, untouched and drags the younger Dean over the precipice with him. 

They stay tangled together, Dean’s face buried in the crook of Cas’ neck while Cas looks over at him and mouths a silent, “Thank you.”

It makes Dean want to be sick. 

One last gift, it was all he had asked for when Cas had told Dean about his plan. One night to have the thing he always wanted but wasn’t able to have. When the day fully breaks, they’ll load up and head out toward the final confrontation. Dean will stand and watch while his idiot best friend sacrifices himself to give him even the slightest chance of taking out Lucifer. Dean hates this plan, hates everything. 

And he realizes as he watches Cas stroke still trembling fingers through the other Dean’s hair, that the only thing he has left to love is going to be dead come nightfall tomorrow. 

Dean hopes he gets to join him.


	23. Time 23: first time Dean didn't want to leave right after and/or first time waking up with someone.

Time 23

Dean jerks into wakefulness pressed against a too hot body in the overly small space next to him. He tenses his body on automatic, too used to sneaking away just before the break of dawn and slip back into the cold, lonely world he calls home. 

But the angel beside him shifts in his sleep, one giant wing sliding over Dean’s body to curl around him and keep him close. The sweet scent of oil slick on Castiel’s feathers causing Dean to relax automatically into the embrace. He knows what staying will mean for them. It’s a declaration of intent for him to still be lying here covered in the oil and come of another angel in the light of day. 

It would make this something serious, something solid. Dean’s never wanted that, never trusted himself enough to think he deserved that kind of affection. 

It scares him. But still, his grace is already singing with hope. His wings twitch against his back, rolling up and over the other angel to curl around him in a protective shell. His dark honey feathers block out some of the light entering into Castiel’s nest and Dean hopes that maybe it will buy him some more time before his dark haired partner swims into waking. 

He’s never been very lucky. Castiel shifts against him restlessly, rubbing up against him and moaning softly before his eyes blink open and he looks up into Dean’s face with an expression of wonder. “You stayed?”

Part of Dean aches that this beautiful creature beside him sounds so surprised. But really, this isn’t their first night together, Castiel’s used to Dean’s comings and goings. He’s never said anything about it, never mentioned he might want more. 

Panic blooms inside Dean’s grace, maybe he misread this, maybe Castiel was happy with the way things have been, now Dean’s here, all but directly proclaiming his desire to mate and Castiel’s going to turn him down. 

“You wish to bond?” Castiel says carefully, his head cocking to the side as he considers Dean like he’s a strange animal. Dean’s feathers puff out all over in alarm, his wings slam outward hitting the rocks on either side of Castiel’s nest making him hiss in discomfort. 

He’s struggling to pull himself together, looking for his cloak before he just throws himself out of the nest and flies away but their bodies are tangled and Dean’s wings just keep hitting everything. This was a horrible idea. 

Castiel’s wings spread wide, curling inward until they’re pressed down around Dean’s cutting off his struggles. “We will need to seek a bigger nest,” he says with a smile as he squeezes Dean gently with his wings. 

Dean melts into the embrace with relief that makes Castiel chuckle. “Mate?” Castiel whispers as his fingers play over the skin of Dean’s back near the sensitive glands that no one has ever touched in all of Dean’s long life. 

“Yes,” Dean manages to gasp before Castiel slides his palms over the glands and stakes his claim. 

“Took you long enough,” Castiel grumbles before kissing the protest right off Dean’s lips.


	24. Time 24:  their first time with Castiels wings out.

Time 24

Sam’s done a lot of weird shit with his brother over the years they’ve been together. Compared to causing and then last minute averting the apocalypse, incest seems a little tame, really in the scheme of things. Sam actually takes a lot of secret pride in the fact that of all the men in history that have teased Dean about his cock sucking mouth, Sam is the only one to ever know for sure just how awesome it really is. 

Dean’s talked a good game his whole life, never backed down from anything, but there was a line he never crossed for anyone, until Sam. So Dean can mouth off about whatever he wants, but Sam knows all it will take to get his big brother on his knees and begging for it is for Sam to spread his legs open and pop the top button on his pants. 

Dean just fucking loves sucking Sam off. 

And Castiel loves watching them. It’s been a slow development of their very odd relationship. Sam and Dean have always orbited each other, never able to break out of their own gravitational pull, and Castiel’s the only person they’ve ever met that’s been willing to not just accept it, but embrace it fully, encourage it even. Sam remembers the first time the angel had sat in the corner and watched them have sex. Sam got off on the thrill of it and Dean skittish like a colt about their audience. But over time it started to feel weird without Cas there keeping watch. Sam had gotten used to looking into those blue eyes as Dean pounded into his ass and he knew Dean had come with Cas’ name falling off his lips just as often. 

The first time the angel had reached out touched the back of Dean’s throat while Dean gave Sam head both of them had come immediately. It had been so unexpected, so good. For there, well…Cas has proven to be a curious and inventive lover. Like tonight, Sam’s the one watching, for now, while Dean sits naked in the center of the bed with Cas impaled on his dick and clinging to him, muttering enochian and begging Dean to speed up. But the pace is slow for a reason, and Cas knows it, he needs to be worked to the edge before he relaxes enough to give them what they want. They’ve been talking about it forever.

His wings. 

Sam’s curiosity ate him alive about it before this whole thing started and Dean finally blurted out how bad he wanted to see them too. Cas had been uncharacteristically shy about the whole thing, saying they were damaged and ugly, but they had blown him off. 

They’re Winchesters; beauty is a different kind of concept for them than for most people. 

Sam feels the electric charge before he sees them; the air in the room being compressed like there is something huge taking up the space. Then they erupt in shadow and smoke all around them, something intangible that’s become as close to solid and real as Cas can manage. Sam lunges forward and buries his hands in the dark, shifting shapes. He hears Cas cry out and feels Dean surge up harder. It’s a race to the finish for Dean now; he’s done his job and held off as long as he can. 

He comes with a groan but Sam’s ready, tugging Castiel off his brother’s softening length and turning the angel, dropping to his knees and taking Cas’ neglected cock into his mouth. He feels Cas jackknife as Dean gropes his wings for the first time. Cas pleads, begs, out of control in a way Sam’s never experienced and when he comes, he doesn’t even try to tug Sam off, the hot blast of pleasure from Cas’ grace causing Sam to come untouched in his pants. 

The angel collapses, exhausted onto the bed. His wings stay out and Sam and Dean trade lazy kisses as they curl next him while he sleeps and groom him.


	25. Time: Sam is a college freshman/sophomore still and it's his first time.

Time 25

Gabriel almost came in his pants the first time he saw Sam Winchester. That had been at the beginning of the semester and Gabriel had struggled to believe that this tall drink of water was only a freshman. Seated amongst a roomful of his peers, Sam had stood out like a sore thumb in Gabriel’s orientation to college seminar. 

There’s a look about Sam that says he’s seen more from life than any kid his age ought to have, even though his body still hasn’t filled out into what Gabriel suspects will be a magnificent model of the human male specimen when all is said in done. He’s already taller than Gabriel. 

Gabriel likes his men tall. 

He had flirted, nothing too serious at first. For Gabriel so little is serious in his life. But Sam hadn’t seemed to pick up on it and they had developed a strange, but appealing friendship. Sam being the freshman that he is and Gabriel being a tenured professor, they might have gotten some strange looks, but Gabriel’s never taken a student as a lover. His reputation is impeccable. 

Until tonight….tonight where he has Sam on his knees and sucking Gabriel’s cock in this mix of sloppy-messy wantonness that makes him think of his brother’s naked so he doesn’t come. Gabriel wants to pour himself down that long throat almost more than anything else in his life right now, but he’s not Sam’s age and doesn’t have Sam’s refractory period. 

He wants to fuck Sam. Sure, maybe he’ll get fired and go to Hell for it later, but right now lust is all he can see. Lust, and the nervously excited young man shaking in front of him as Gabriel strokes his way through Sam’s mess of brown hair. 

“I’ve never…” Sam stammers. 

“I gathered,” Gabriel chuckles. But when Sam draws back to give him a hurt look Gabriel drops to his knees and kisses it off his face. “What do you want from me, Sam?”

There’s a pause, then Sam is unbuttoning his jeans and dragging them off, tugging his shirt over his head, it’s not until he’s totally nude and on all fours in front of Gabriel’s body that Sam whispers, “Teach me.” 

And Gabriel’s always loved to teach. Slipping a finger against Sam’s ass proves that his pupil doesn’t have a problem doing his homework. “Lube?” Gabriel asks as he works a finger into Sam’s slightly loosened hole. 

“I wanted to know what it might feel like,” Sam mutters into his crossed arms. The idea of Sam experimenting makes Gabriel hot all over. 

“What did you use?” Gabriel asks as a second finger slides in along side the first. 

Sam flushes all over like he’s on fire. “Please don’t make me answer that.”

“Of course you don’t have to answer,” Gabriel grins as he slowly, so slowly drags his fingers free of Sam’s body. “We can talk about something else.” 

“Fuck! Sam barks out wiggling his ass like that will put Gabriel’s fingers back where he wants them. “I hate you…..a cucumber, okay? A big fucking cucumber while I thought about you. Now please!”

Gabriel’s already slicking his dick with the lube from Sam’s pants pocket before Sam even answers. It only takes him a second to scoot closer and slide in deep. Sam whimpers brokenly and comes after two strokes. Gabriel doesn’t last much longer. 

They sprawl on the carpeted floor of Gabriel’s living room afterwards. “We need to get you better sex toys,” Gabriel comments. 

Sam sighs, long suffering and exhausted, but when Gabriel reaches out to touch him Sam curls into his side without hesitation. “Love you,” Gabriel whispers against his temple. 

And he does, more than anything.


	26. Time 26:  First time after Jessica

Time 26

Sam never thought about falling in love again. It hadn’t been an idea he could cope with for so long that eventually it started to feel like a dream he had when he was young. A dream that had turned into a nightmare, losing your fiancé in a house fire will do that to you. 

But eventually, after years of vicariously living through his older brother’s conquests, Sam finally came to the point where he couldn’t hold back the need for contact anymore. He didn’t want love, that was never the idea, but Sam’s a guy, and he has needs, and let’s face it, his hand wasn’t doing it for him anymore. 

Lucifer had been…an opportunity. Hell, Sam doesn’t even know the guys real name. It’s just a nickname he refers to his fuck buddy as because the guy looks down right evil most of the time, even when Sam’s sucking him off. So yeah, the guy is prickly, nasty even most of the time, but he knows how to make Sam feel things he never thought he would and gives as good as he gets. 

It’s enough….or at least it used to be. 

But after three months of decent hip grinding orgasms and blow jobs to die for, Sam’s starving for something more intimate, and yeah, he totally knows that’s an issue because he’s made it pretty clear from step one that actual fucking was never an option and now changing his mind is going to make him look needy and stupid. 

But Lucifer’s two fingers into his ass before he notices that Sam’s rocking harder back onto his digits than into his hot-wet mouth. His head comes off Sam’s dick with a pop and he growls out, “This isn’t what you really want tonight, is it?” 

Two slick fingers becomes three, and Sam groans out as he rocks his hips back onto the welcome thickness opening his body. His face flames with color and thankfully Lucifer doesn’t really seem to expect him to answer. “Okay then,” the other man murmurs. “Turn around.” 

Sam hisses at the feeling of being empty, scrambles to slide off the couch onto his knees and lean over the cushion he was just sitting on. He’s shaking, nerves raw and wired as he hears the shuffle of clothing and the crinkle of a condom being unwrapped and rolled down. Then Lucifer’s body heat is right up behind him and the weight of his dick pressing inside. Sam moans, rocking back for more, harder, needing to be filled up and fucked open. 

Lucifer doesn’t disappoint him, hand tangled in Sam’s hair as he sets a punishing pace. Sam comes off the feel of his thrusts alone, splattering come all over his couch in a horrifyingly short amount of time. 

He feels exposed now, vulnerable, and whimpers as Lucifer slips free of his body and slides away. 

There’s a pause, this is where one of them just sort of leaves, and God, Sam doesn’t want that tonight. Not at all.

“Would you like for me to…go?” Lucifer says softly, his tone uncertain. 

Sam pushes himself up, turns around and faces his…lover? Is that what they are?

“No.” He finally answers. 

Lucifer settles back, posture relaxing like that might have been the answer he was hoping for. “Very well then.”

Sam swallows, holds out his hand even though he feels utterly ridiculous, and says, “Hi, I’m Sam. What’s your name?” 

The other man smiles, and for the first time it seems genuine and warm as he reaches out to clasp Sam hand.


	27. Time 27: first time coming together as a flock after the end of the war

Time 27

His wings ache as he flies for home. Dean’s fought hard, held off the forces of Hell during the uprising with all of his strength. Now he just wants his family, wants to lose himself in the bright spirits and sweet touches of his mates. 

Assuming they all survived. 

He’d lost sight of Castiel in the first wave of attackers. Gabriel launching himself at the oncoming horde with the vengeance befitting an archangel as Sam remained at his back throughout the ordeal. 

Dean sweeps into his nest with a heart full of fear and hope and stumbles to a halt at the scene he finds in front of him. 

Sam sprawled on his back in the center of their nest, naked and sweating as Gabriel sucks him down, messy and eager as he’s ever been. The archangel’s wings spread out to fill up the room in his pleasure, oil leaking down his back as he gives himself up to being with his mate. Dean groans, relief rolling through him at the sight. 

He knows they wouldn’t be this way together if his other mate was missing. 

“Castiel…” he calls out softly, Sam’s eyes opening to catch Dean’s gaze and he groans and fills Gabriel’s mouth. 

“Hello, Dean,” Castiel’s rich voice brushes across the feathers on Dean’s wings as he turns, catching sight of Castiel’s too blue eyes before the smaller angel presses in close and nuzzles his way in for a kiss. 

“I’m disgusting,” Dean says by way of warning as Castiel starts to dig his way into the sensitive underside of Dean’s feathers. 

“Frequently,” Castiel chuckles and laughs outright as Dean pounds on him with his wings. “You need a good grooming.”

“I’m so tired,” Dean admits, grateful to be able to let his guard down and trust his mates to protect him. 

“Come here,” Gabriel says from where he sprawls lazily next to Sam in their nest. “Come home and let us take care of you.” 

Deans distantly aware of Castiel unbuckling his armor, he knows he crosses the room and collapses onto into the center of his nest on his own. But it’s all a blur compared to the sweet brush of his mate’s wings and the tender kisses they press into his skin, healing his wounds and soothing his pain. 

It’s like melting as they take him apart and help him reform. Their grace blending, swirling, and becoming one as they tend to each other. 

War is horrible, Dean hopes to never take part in it again. But being here, being with those he loves most reminds him of what he fights for and gives him strength to face the dawning day.


	28. Time 28:   first time after Gabriel is brought back to life

Time 28

Gabriel’s…different when he comes back. He seems smaller somehow, weaker, like something Sam wants to protect and tend to. It’s a weird feeling for Sam. He doesn’t really like Gabriel all that much even though he has developed something like admiration for his moxey. Gabriel is a ballsy little fucker. 

A ballsy little fucker who looks more and more like he needs a hug. 

So it’s late, hell, maybe it’s early, one night when Sam finally just reaches out and draws Gabriel’s too tense, too thin body up against his own. The angel hisses at the contact, holds his body rigid against Sam’s before melting against him with a ragged and pitiful moan. His arms slide up to wrap around Sam’s body, shaking like he has a chill that just won’t let go and so Sam holds him tighter, works his hands up under the jacket and shirt that Gabriel seems to never take off and brushes against skin that Sam always thought would be hot and instead finds too cold. 

It’s probably the shiver that Gabriel makes as Sam skates his hands over his ribs that does it. Sam won’t ever be sure exactly how they end up with him picking Gabriel up and carrying him to the bed with Gabriel’s tongue pressing against his tonsils. Then their clothing sort of just…disappears, and for all Sam knows Gabriel just wills it away. 

He’s shocked when Gabriel lets his wings out, light and heat flowing out into the room around them as he parts his thighs and invites Sam inside. Sam’s going to fuck and an angel, an archangel, his mind stumbles over the concept even as he dips his fingers into Gabriel’s already slick body and stretches him open easily, like Gabriel’s already been worked open and has just been waiting for Sam to fill him up. 

So he does, slides in deep as he bends over Gabriel’s breathless form and sucks marks along his neck and shoulders. 

“Sam,” Gabriel pants again and again as Sam thrusts. Gabriel comes before he does, seizing up around him with a whimper causing Sam to follow behind. 

Afterwards Sam keeps holding him, soothing his fingers through what he guesses are feathers, with angels it’s kind of hard to tell. 

“Stick around,” Sam says softly. It’s half a question, half a request. 

Gabriel nods into his neck and lets out a breath is sounds like he’s been holding for a really long time.


	29. Time 29:   Nervous

Time 29

“He’s watching you again,” Dean chuckles. 

Castiel turns to glare at his best friend as he snarls, “Stop it!” 

“You should just go talk to him,” Dean encourages with a shrug. “So he’s kind of creepy, you’re into it. That much is obvious.” 

Castiel groans inwardly as he follows Dean’s gaze to the puffed up outline of his own feathers. It’s humiliating, Castiel hasn’t lost control of his wings like this since he was teenager. But there they are, exposed and trembling, every feather leaning toward Lucifer’s imposing form basically begging to be fucked. 

He’s not easy, even if his wings are telling another story. 

“No,” Castiel sighs. “It would be inappropriate for me to approach him. You’re human, you don’t understand. Angelic mating rituals are specific and Lucifer is far out of my league. I’m just a hunter.” 

Dean’s silent for a long time and Castiel finally turns to regard his oldest friend with concern. He knows Dean doesn’t like the stigma Castiel has to suffer with for being his partner. Dean’s open minded, especially for a human, and perceived inequality upsets his soul. One day, Dean will make someone a fine mate; Castiel suspects he already has his eye on someone. Castiel will likely spend the rest of his life isolated from his own kind. 

But that was his choice; he knew the consequences when he joined Dean and Sam on their endeavor to locate their lost father. He has no regrets. 

“Did Lucifer miss the memo then?” Dean suddenly enquires. “Because he’s coming over here. Time for me to exit.” 

Dean dashes away before Castiel can scramble to stop him, leaving him alone with the imposing archangel now standing before him. 

“Can I help you?” Castiel stammers, dutifully ignoring the way his wings fidget and arch toward the other angel. 

“I was going to ask the same of you,” Lucifer comments softly as he reaches out one finger to trail along the bristled edge of Castiel’s left wing. He jerks, slamming his wings down against his back so hard Castiel loses a few feathers in the process of jerking himself away. “You need a good grooming,” Lucifer adds as they both watch the feathers drop to the ground all around them. “Does your human not perform this task for you?” 

“Dean does as well as can be expected for a being without personal knowledge of wings,” Castiel defends even as he can hear his heart booming inside his chest. 

“You deserve better,” Lucifer says as he steps closer and Castiel steps away. “I make you nervous.” 

“I’m anxious by nature,” Castiel retorts, backing up further only to bump into the tips of Lucifer’s huge wings as they curl around him slowly. 

“Are you frightened of me?” Lucifer asks. His tone so saddened that Castiel stops his retreat. 

“No,” Castiel assures him. “I’m just confused by your attentions.” 

“I want to groom you,” Lucifer clarifies. 

“But why?” Castiel squeaks, embarrassing himself even further. He feels his cheeks glowing red. He does need a grooming, badly in fact, his wings are filthy. 

“Because I’m attracted to you,” Lucifer smiles then, more genuine than Castiel has ever seen him. “I just have better control over my wings than you do. You interest me, and it’s been a very long time since I felt like this.” 

Castiel takes a deep breath, relaxes his wings until they drop toward the ground open and vulnerable to the other angel. “I should warn you,” he rumbles. “I’m likely to come; it’s been a long time for me.” 

Lucifer looks positively enraptured. 

“I’m certain you will,” he murmurs as he steps closer and leans into Castiel’s body. “Several times in fact, by the way your grace is already singing for me. I’m looking forward to it.” 

Honestly, so is Castiel.


	30. Time 30:  The first time Castiel has to deal with an injured Dean when human in their new home.

Time 30

“You should see a doctor,” Castiel stammers as he follows Dean out of the garage and into the kitchen. 

Dean’s bent over the sink examining his hand under the cool water of the faucet while Castiel paces and wrings his stupid, useless, human hands behind him. 

“I don’t need a doctor, Cas,” Dean snorts as he focuses on trying to determine the damage. 

“You could have internal bleeding; your bones might be broken. What if this has damaged your hand in such a way as to make you unable to use it?” Castiel is aware on some level that he’s ranting. Human emotions have turned out to be, by far, the most difficult thing about being human. He’s found he enjoys eating and drinking, even finds some level of comfort in the way he sometimes drifts off against his will in front of the television at night. Waking is a unique experience but having the option to roll over and rest in the soft bed in his room is wonderful. Even relieving himself has some small measure of pleasure, especially if he really has to go. 

But these strange feelings that rear their head at the most inopportune and unwelcome times are truly frustrating. He is aware it would be more helpful were he to be able to calm down, to squash this horrible irrational fear that he’s damaged Dean beyond belief, and do something helpful. But he can’t, he’s…afraid and though Dean is the injured one it’s Castiel who wants to be comforted. 

Emotions are very annoying. 

“Dude,” Dean sighs that long suffering sigh that he does when Castiel is being overly dramatic. “You accidentally smashed my hand under the hood of the car. It happens.” 

“Then why are you running your hand under the water? Did it burn you?” Castiel tries craning his head around Dean’s hunched shoulders only to have his friend rear back and look at him as though he has lost his mind. 

“My hand’s dirty, Cas!” Dean exclaims. “I’m just trying to see if this is a bruise or some grease. You need to chill.” 

Castiel melts against the countertop with a groan. “I’m sorry, Dean.” Another apology, one added to the thousands already piled up between them. 

But Dean grins, wraps his somewhat swollen hand around Castiel’s neck and squeezes just enough to tickle to make Castiel smile against his will. “It’s nothing, Cas. But you get to make dinner now. I’m taking the night off.” 

Castiel wants to kiss his best friend suddenly, an urge he’s never really felt before. Heat blooms inside his chest and he feels himself flushing, Dean must notice his pulse rate rising as he loses control of himself. The teasing grip on his neck softens into a gentle caress and Castiel gasps. Dean leans in hesitantly, pressing his lips to Castiel’s temple before stepping away and muttering, “I need some ice.” 

Castiel stands still, cataloging these new sensations and wondering what else Dean might be able to make him feel.


	31. Time 31:  Tears.

Time 31

Some nights he wakes up screaming. Castiel blinks awake clinging to the side of the mattress in his room, covered with sweat and trembling all over. His throat aching with the noises he knows he must have been making. 

The Winchesters do him a kindness by pretending it’s not happening. Though there are books upon books that could be written full of the information they know about each other and never say. 

Sam has his own night time issues, Castiel and Dean often hear him talking to himself, reciting prayers or poetry, arguing with images his twisted mind presents when he thinks no one is watching. The guilt Castiel feels is immense. His fault Sam is the way he is. Castiel’s failure, one of so many things he’s failed at. He doesn’t deserve their kindness. 

Doesn’t know how they find themselves able to forgive him. 

Sam had once told him he had always felt the need to be punished for setting Lucifer free. That he often thinks of his fractured soul as a gift, because of it, he no longer feels guilty. He’s paying for what he caused. 

Castiel wonders what he will need to happen to him in order for him to no longer feel the soul crushing weight of guilt. But maybe he doesn’t deserve that freedom, after all, Sam Winchester is a good man, and Castiel is The Fallen One. Maybe he’s still falling. 

Tears…he hates this weakness that overcomes him on these long, lonely nights. He’s too tired to get up, to soul weary to put on his mask and walk out into the living room. He wants something, something he can’t put a name to. He aches so much inside. 

He’s not sure how much time passes before the door to his room is opened and Dean slips inside. His friend doesn’t bother to turn on the light instead slipping down to curl beside him on the bed where Castiel has shrunk in on himself shaking and sobbing. 

“The screaming I’ll ignore,” Dean whispers as he wraps his warm arms around Castiel’s quivering body. “But you’re sobbing so loud the walls are shaking.” 

“I’m sorry, sorry,” Castiel chokes out around heaving breaths and hiccups. 

Dean snorts, tugging them both until he’s over on his back and Castiel is resting, facing him against his chest. “Shut up, Cas. I didn’t come in here to yell at you.”

He soaks Dean’s shirt, unable to stop crying. But for some reason he feels better as he drifts back off to sleep. Dean’s heartbeat a steady thrumming reminder that he’s not as alone as he feels.


	32. Time 32: Chocolate

Time 32

The first time, well, okay, maybe not the first time. Dean possibly slipped him some before he fell and Castiel just overlooked it because he deemed it unimportant. 

Anyway, the first time Dean gives him chocolate is after Castiel has spent a week wracked with horrible nightmares. He wakes up usually around three in the morning screaming his head off and then disintegrates into wild sobbing from there. Most nights it’s Dean that comes to him, hauls him in tight against his chest and lets Castiel cling to him in what is probably a very humiliating manner before he finally gives into exhaustion and falls back to sleep. 

But last night Sam had been the one to stumble into his room and cradle Castiel against his chest. He hadn’t thought at the time to ask where exactly Dean was and why he wasn’t coming, but this morning the rubbed red and raw skin around Dean’s eyes had told Castiel everything he needed to know on the matter. Dean hadn’t come for him because Dean was busy having a melt down of his own. 

They don’t talk about it…ever. It’s not the winchester way. 

But tonight, as the sunlight creeps away and the moon rises in the sky Dean settles down next to him on the couch and pushes a partially unwrapped bar of chocolate over toward Castiel’s leg. Sam is suspiciously absent and Castiel ponders why this moment is considered to be so momentous that he would need privacy. It’s food, after all, and humans eat in front of each other with very little discretion even when what they’re eating is disgusting. 

“It’s dark chocolate,” Dean murmurs as if Castiel understands the difference. “You like salty stuff so I thought you might like it better if it was richer.” 

Castiel looks at him for a long time before dragging the wrapper closer and breaking off an edge of the chocolate that’s been exposed. There’s a cold ball of tension coiling in his gut as he lifts the bit of chocolate to his mouth. He almost doesn’t want to try it. Dean’s looking at him so intently as if he expects something amazing to happen. 

Castiel’s familiar enough with that look on his friends face to know it mostly leads to him disappointing Dean in some inexplicable way. But never-the-less, he forces himself onward and closes his lips around the bit of candy bar. 

For a moment there’s nothing, maybe his mouth is too dry. But then, once the slightly bitter confection starts to melt, it’s an explosion of richness on his tongue, making Castiel eyes slam open in surprise before slipping shut in bliss. A long groan of pleasure escapes him before he can stop himself, sounding wanton and needy over something so stupidly simple as a bit of sweet. 

When he collects himself, already reaching out for more, his eyes slide to Dean’s. For the first time in a long time Castiel sees nothing in his gaze but pleasure.


	33. Time 33: after John’s death.

Time 33

He wants it to just be physical. 

If it’s just a good fuck, a one-off for both of them then it doesn’t really count as incest. Not really, not to Dean. 

But they both know it’s more than that. Sam probably knew the minute Dean pinned him back against the horrible motel room wallpaper and pressed in close for their first, really awkward, kiss. Both of them stumbled through it like blind men trying to drink from a foot peddle fountain after a week with no water. It’s was ugly, but it got the job done. Things had gotten easier after that, clenched hands and sweet friction against their dicks from too tight jeans. Dean wanted it rough, didn’t want it to feel like comfort even though it’s what he wants more than anything. But Sam, fucking emo-ass Sammy, can’t do anything without his heart being involved and by the time Dean’s wrestled them both out of their clothing and angled them toward the bed Sam’s turned his yanking, clenching, grinding, desperate movements into slow kisses, soothing strokes of his hands down Dean’s sides, long gazes that get held even when everything in Dean screams for him to look the other way. 

It’s not what he wants, but Sam never cares about what he wants. He just gives Dean what he needs even when it’s the exact opposite of what he thinks he might be asking for. 

He should have known that before Sam dropped him down onto the mattress. Dean should have guessed how this was going to go when Sam took the lube for himself and slipped down to suck Dean’s dick like it was the best lolli pop ever in the history of mankind. But, sadly, and this says a lot for his emotional states more than anything else, it’s not until Sam’s sliding down on top of him, taking him inside and clenching their hands together over Dean’s head that Dean understands how much they’re both hurting.

This isn’t about sex. It’s not a one-off. It’s love, hot and hard and painful between two people that just lost the center of their worlds. It’s Sam’s tears sliding off his chin to drop onto Dean’s chest while he rocks too fucking slowly onto Dean. It’s the sob that sputters out of Dean’s mouth when he’s expecting a moan instead. Then one leads to two, to four, to him gasping and whining and Sam cupping his face and whispering, “It’s okay. I’ve got you. I’m here.” 

It’s Dean coming apart in a way he didn’t expect, on the inside of himself that’s like the worst and best orgasm he’s ever had. 

It’s Sam, sweet, stupid, Sammy, still holding him when dawn comes on Dean’s first day without their dad.


	34. Time 34:   first time they make love and/or first time Gabriel lets his mask down and lets Dean see him for exactly who he is.

Time 34

Dean’s not sure what exactly he’s expecting. Gabriel’s not a jerk, not exactly. But he’s always been kind of prickly to everyone. He keeps everyone at a distance, all the time. So needless to say, he was shocked when Gabriel started hanging out after shop class to watch Dean sweep up. 

It’s not a job he gets paid for or anything, but Mr. Singer’s always been like a second father to him and so it’s just something he does. Gabriel doesn’t help, that would give the impression he’s a nice guy, which Gabriel seems to want everyone to think he’s not. Dean doesn’t ask any questions, and Gabriel doesn’t offer explanations. 

It goes on like that for two weeks. 

Then, on a random Friday when Dean’s finished sweeping up and is heading over to grab his book bag and hit the door going home, Gabriel blurts, “Are you busy tonight?” 

It makes Dean pause. He’s not out, not exactly, but he’s not a liar either. Still, it’s hard to tell if this is a date offer, a ‘let’s have sex in the back of your car’ offer, or an ‘I need a ride somewhere’ offer. “Why?” He settles on a question because he’s just not sure what the right answer is. Clearly, it’s a bad choice because Gabriel clams up hard, stiff backed and glaring as he charges toward the door grumbling, “Forget it.” 

Okay….but what the hell, Dean’s curious, and Gabriel’s…interesting. 

He puts his hand out and holds the door shut so Gabriel can’t get out. “No.”

There’s a long intake of breath, like Gabriel’s preparing for the rant of a lifetime. Dean’s heard them before, directed at other people, and Gabriel can be a mean son-of-a-bitch when he wants to be. It’s easier to cut him off at the pass. “I mean,” Dean clarifies, “No, I’m not busy.” 

Gabriel literally deflates. “Oh. I’m…okay. I guess I didn’t read that right.” 

“Yeah,” Dean nods. “So, I was just trying to figure out what you wanted to do…with me.” 

And oh, he blushes, Gabriel’s amber eyes flickering all over the room, everywhere but landing on Dean as he shifts from one foot to the other. He coughs, swipes a hand over his face only to peak out from between his fingers and glance Dean’s way. 

He’s not so scary. Not now. 

Dean reaches out, tugs Gabriel’s hand off his face and presses a kiss to the slightly sweaty palm. Gabriel shivers all over; he turns their hands so their fingers tangle. 

“I want to trust you,” Gabriel whispers, like he’s worried someone might hear. “I’m tired of being alone, and you’re not scared of me like everyone else is.” 

It’s on the tip of his tongue to point out their classmates are scared because Gabriel can be a real asshole, but Dean bites it back. He’s never seen Gabriel like this, open, honest, uncomfortably shy. It’s a good look, one he wants more of. “Let’s go get a burger,” Dean offers with a gentle tug of his hand. “I want to know all about you.” 

They walk off down the hallway; Dean tugs Gabriel closer, slips an arm around him and enjoys the way Gabriel’s smaller frame fits against his own. Gabriel talks, Dean listens. 

He likes what he hears, especially the things Gabriel doesn’t say out loud.


	35. Time 35: First time without condoms.

Time 35

Sam hates to admit it. He wants to be the good guy and swear he can’t tell a difference. It’s the right thing to do. The good thing. The safe thing. 

But fuck it. He’s so so so tired of being the good one. 

This feels fucking fantastic. It’s like he’s been stumbling around in the dark his whole adult sexual life and this, this is Castiel finally handing him a flashlight to see by. Sam’s always been careful, okay, so maybe when he was robo!Sam he wasn’t, but that was totally not his fault. He never wanted to accidentally knock some poor girl up when he was a kid and get stuck living in some small town nowhere taking care of child when he still was one. Then with Jessica, well, she had plans and he had plans and she had an allergic reaction to birth control and so they used them, every time, the condoms. Sam had always thought once they were married and stable…but that never happened. 

Then he found out about the demon blood, and so help him, he was never going to risk passing that horror onto a baby without understanding what it might become. So yeah, Sam’s list of experiences without condoms are pretty small. He’d convinced himself it didn’t matter. 

He’s a dirty filthy liar. It matters a lot. 

Cas is hot and tight against him. Just like he always is, but it’s like Sam’s really feeling it for the first time. The slick slide of the lube is making everything between them wet and messy and fuck it’s taking everything Sam has to not come right now just from thinking about the concept that when he does he’ll actually be filling Cas up instead of some stupid latex. He’s going to come in Cas. 

He’s going to come…in Cas.

He’s. Going. To. Come. In. Cas. 

NOW!

“Oh fuck!” Sam groans as he tips over the edge into orgasm so suddenly he’s totally unprepared. It’s too fast, over before they even started really and he knows Cas has to be disappointed in his performance. But maybe if they take a little break he’ll be able to go again. 

It takes him a minute to get it together enough to understand that Cas is squirming beneath him, arms reaching out to drag Sam down as he presses frantic kisses all over Sam’s face. “You came,” Cas pants out. Sam flushes in embarrassment. “I could feel it. I could feel you coming inside me.” 

And God, if he could come again right now Sam would. 

He shoves forward just a bit, still hard enough to make Cas spasm around his dick and the mess he made inside his lover. Cas whimpers. He’s close; Sam’s learned the signs in the months they’ve been together. He drags his lips up Cas’ throat brushing the bottom of his ear and he whispers. “Filled you up. Mine.” 

The words and a single finger rubbing along the slit of his dick is all it takes for Cas to keen, toss his head back, clamp his thighs around Sam’s hips, and come so hard he hits himself in the chin with his own come. 

“Yours.” He pants in the aftermath. 

Sam hums. Pleased.


	36. Time 36: Gabriel/Dean/Gabriel.

Time 36

It’s like being trapped between to lions fighting over a piece of meat. 

Dean’s been in worse situations, honestly. 

Gabriel’s pressing him back against the other Gabriel’s chest. Dean’s sandwiched in between to the two of them, pinned down, trapped, strapped in tight by four arms and two hot bodies. Identical copies of each other, the original, and the...other. Just the same as the first, though maybe even more mouthy, Dean’s lost track of which one is which. He’s too focused on the hot press of ones mouth on the back of neck, his dick hot and thick pressing against the small of Dean’s back, rubbing wetness across his spine as slick fingers probe him open and fill him up. 

The other Gabriel, the first Gabriel, Dean thinks is torturing his nipples, pinching and twisting, flicking and tugging, making Dean whimper, making him squirm. Gabriel’s head dips lower, across his stomach, licking and sucking a trail of wetness down to where Dean is aching, straining, needing him most. The moment the hot, wet mouth of his lover slides over his length Dean bucks moaning, as he reaches out to grasp and hold onto to any part of the two other bodies in the bed with him. He’s lost, confused and frankly a little bit frightened. They had planned this, discussed it, hell, Dean had been all for it. But now, as it’s happening it feels like too much, too fast, he wants comfort, wants his lover, the one he’s familiar with, to hold onto him and tell him he’s safe. 

Safety is something Dean’s learned to cherish more than anything else in his short life. 

“We’ve got you,” the Gabriel behind him whispers into his ear as twisting fingers slip free of his body and the too familiar feeling of Gabriel’s dick pushing it’s way inside of him. It’s so strangely familiar that Dean is almost convinced he has it wrong, maybe the one behind him is the real one. “We’re both the ‘real’ one,” the Gabriel behind him murmurs breathlessly while the one in front, still sucking him off moans around his dick in a way that is way too distracting. “Same memories, same feelings, same body; it’s not one Gabriel and a copy, Dean. It’s me, both of us, just me. I love you. You’re not alone.” 

It’s all it takes for Dean to drop his head back against Gabriel’s shoulder and let it happen, let his lover, the both of them, take care of him, support him, make him come. 

And he does, keening into the air into the air of the motel room, crying out wordlessly, as he tips over into bliss. He’d like to say he remembers the next few moments, but honestly, Dean thinks he’s out for a while. When he comes back to himself he blinks at the sight of his lover, wrapped up with himself, making out on the bed next to him. It occurs to Dean then, in his hazy post orgasmic state of mind that he should keep both these guys around. 

Shit they’re hot.


	37. Time 37: Older virgin neighbor Gabriel.

Time 37

They moved in last September. Sam’s putting the finishing touches on his second and final year of community college. He and Dean had talked about it and decided right out of high school that their budget just couldn’t take Sam going directly to a four year school. 

Honestly, he didn’t mind. Since their dad died he and Dean have been two halves of the same whole and Sam hadn’t really wanted to leave Dean behind. It’s been nice settling down roots, make friends with the neighbors. 

Especially Gabriel. 

They aren’t really neighbors, strictly, Gabriel’s back yard backs up to Sam and Dean’s so he doesn’t even technically live on the same street. But he and Sam have struck up an odd sort of friendship, Gabriel being almost fifteen years older than Sam and coming from a highly religious background. The guy had been a priest until four years ago for fuck’s sake. 

Sam had asked him once after a hot afternoon of cutting down a tree that took out their shared fence after a storm. They had been on their second or maybe third beer and he had just blurted it out before he could stop himself. Gabriel had just kind of smiled at him before murmuring, “I had to leave, impure thoughts.” 

And oh, Hell. Now it’s all Sam can think about. He wants to know what exactly Gabriel had been thinking about that was so impure, and more importantly does he think about wanting to act out those thoughts with Sam. If he did, Sam would jump on that in a hot second, Gabriel is exactly the kind of guy Sam loves. 

Or could love, if given half a chance. So imagine Sam’s surprise when Gabriel asks for help with tearing out some carpet and that translates into Sam helping Gabriel lose his virginity. 

“Well,” Gabriel had shrugged, full of false bravado. “I don’t want to be a forty year old virgin and you keep staring at my crotch.” 

Sam can’t even argue with that. He does keep staring. It’s hard to be discreet when he’s so tall and Gabriel so…not tall. 

The way Gabriel opens up for their first kiss is a little bit like going to Heaven. And Sam knows he’s probably going to Hell for just thinking about doing this, much less acting on it. He doesn’t care. 

He’s expecting there to be shaking hands and nervous heart pounding, he just wasn’t expecting it to be him that felt that way. Gabriel just strips him of his clothing slowly, calmly, and whispers into Sam’s ear, “Tell me what you like. Show me how to please you.” 

And fuck, Sam’s not experienced enough yet to answer him. He ends up bottoming, something he hasn’t ever done, and in a way it’s a first time for both of them as Gabriel stretches out along his back while he’s buried deep inside and groans like he could die right then and go happy. 

Sam’s pretty sure he could too. Then Gabriel starts moving and it just keeps getting better and better. 

He comes apart sweaty and screaming so loud Sam’s a little afraid Dean will come rushing over thinking Gabriel is murdering him. He’s so focused on the fear that the back door is about to be thrown open that it takes him a minute focus on Gabriel crying against his back. 

“Are you alright?” Sam asks as he rolls them over and drags him in close. 

Gabriel snuggles against him like he’s trying to climb inside Sam’s skin. “They said I would regret it, I would repent this sin of need…”

Sam tenses. 

“They were so stinking wrong,” Gabriel huffs against his collar bone. Then he’s kind enough to join in as Sam bubbles over with horribly inappropriate laughter.


	38. Time 38: Dean finally believes Gabriel might give a shit about him. And lets him top him.

Time 38

It’s a twist and a stretch just to the left of uncomfortable inside of Dean. He hisses. Fuck. He’s never going to rush this part again…ever. Didn’t realize how vulnerable one finger in your ass could make you feel. Never thought much about how this would feel outside of the physical. 

It hurts, a little, not too bad. Gabriel’s poured so much lube on his fingers Dean’s pretty sure it’s like an oil spill on the sheets. It’s more than enough to ease the way, but he’s so tense and Gabriel’s so nervous they’re still kind of making a mess of things. 

“I love you,” Gabriel breathes out against his bare skin and Dean feels something in him give just a little bit more, relax just enough, to turn the friction drag of Gabriel’s finger into a slide that makes him groan instead of pant through. 

So good, all of this. So much better than he had ever hoped for. 

“So tight,” Gabriel murmurs. The slow drag of his finger in and then out of Dean’s body suddenly seeming much more wanted than intrusive like it had only a second ago. “So beautiful.”

Dean hates that he blushes, blood pouring into his face and down his chest making all his freckles stand out that much more. Gabriel doesn’t seem to mind at all. His low hum of pleasure and something that sounds suspiciously like contentment vibrating against where his cheek is pressed to Dean’s back. 

Another finger slips right in like it belongs there and Dean widens the stance of his knees gasping as Gabriel pushes in slow and deep and rubs against something that feels so fucking good he whines and pants, so hard he wants to die right now. 

He knows Gabriel’s watching, eyes glued to where his fingers are pressing in and in and in. Dean’s beyond believing that it’s anything but hot, Gabriel’s gaze fixed upon this part of himself he’s never wanted to share with anyone before. 

Then three fingers, oh, a little burn there now, filling him up, making him squirm. So good, so everything. 

“Dean,” Gabriel’s voice sounds as shaky as his hand pressed against Dean’s hip. “I need you, please. Be sure.” 

Dean huffs out a laugh. This might be the only thing he’s ever been sure of in his life. “Love you, need you. Gabriel, please.” 

There’s a flurry of movement, Gabriel biting the ridge of his spine as his fingers slide free. Dean whimpers totally exposed now, feeling emptier than he’s ever felt. But then heat against him, Gabriel, thick and hard, pressing inside. He hears the way Gabriel’s breath is rattling, and the idea that this means just as much to him as it does to Dean is what undoes him. He comes at the first brush of Gabriel’s fingers against his dick, explodes across the sheets before Gabriel even gets fully seated and then glories in the way his lover grabs his hips with a desperately choked off cry and just loses himself in his own pleasure. 

Gabriel out of control will never not be hot. 

They’re totally doing this again.


	39. Time 39:  Anonymous hook up.

**Summary for the Chapter:**

> Friends in a group go to a fetish club where they have a game where two people are put blind folded into a room and can't come out for one hour. They're allowed to do whatever they want as long as they remain blind folded. A challenge of a simple kiss turns into the hottest sex either of them have ever had.

Time 39

Maybe Dean spent the first fifteen minutes feeling his way around the wall for the door. 

Maybe he spent the next ten sitting in the corner, he thinks it was a corner, contemplating how exactly anyone would know if he took the blindfold off. 

He’s pretty sure they wouldn’t. Pretty sure. 

But then all thoughts of wiggling his way out of this are interrupted by a body, a very male body, tripping over his pulled up knees and falling into his lap with a muffled grunt. 

It seems he hadn’t been the only one thinking of cheating. But now that the other participant has literally fallen into his lap it’s kind of hard for Dean to not be curious. 

Hot, anonymous, sex could be a really good thing. Work has sucked recently and having an undying crush on your very straight, possibly headed to the priesthood, roommate is starting to get to him. 

Maybe this can distract him for a while. 

It starts as nuzzling more than anything else, Dean won’t ever admit to it but he’s a snuggler; loves the freedom of being able to touch how and when he wants without needing an explanation. It’s the emotional side of intimacy he’s not well versed in. The physical he’s got covered. The man in his lap startles, body tense like board before letting out a ragged groan at the first press of Dean’s lips against his cheek and melting. 

It’s only an hour, Dean figures he needs to get the show going since by his estimation they only have about half that left. It only takes a few tugs on the guy’s shirt before the other man starts stripping, Dean helps him along and groans happily when cool hands push his shirt up, unbutton his pants. This is going perfectly. This was an awesome idea. The other man sucks brutal marks into Dean’s neck, just like he likes it, tugs his hair and moves Dean around just on the right side of rough for Dean to remember this isn’t a girl he’s with, someone his size, someone who can take his strength and give it back to him. He buries his face in his partner’s neck and rolls them around onto the floor wrestling almost playfully before finally coming out on top. Something about the way the guy smells is kind of familiar but Dean’s hazy with alcohol, can’t really place it. He’s thankful the build is all wrong to be his boss, or his brother, because their friends are sick fuckers sometimes and that would right up their alley to toss them half drunk in here together. 

The guy beneath him groans again, his thighs spread and Dean can feel the wet tip of his dick slide next to his own. “That’s it,” Dean growls out as he settles his hips tighter against the other body. “Good boy.” 

The other man freezes, everything going taught like he’s thinking, just for a moment, of tossing Dean to the side and running like hell. Maybe not one for dirty talk, Dean bites his lip as he waits. Doesn’t want this to end, not in rejection; he gets that enough in his real life. 

But then arms lift from where a moment ago they were holding away to wrap around his back and tug him closer, hold him tighter. Their dicks slot together so fucking perfectly and then Dean’s thrusting, rubbing them together and losing himself in that feeling he’s been wanting so badly for so long. The man under him clings, hips thrusting up as Dean pushes down, the pace uncoordinated suddenly, frantic, as he gets close. “Dean!” being gasped out of the stranger’s mouth as he comes into the pace between their bodies. 

Oh God, “Cas,” Dean chokes out, something swirling inside him at the idea he’s doing this with the one fucking person he’s been wanting for so long. His orgasm hits like a truck, Dean shaking, chanting, “Cas, Cas, Cas,” as he comes. He drops his weight onto his roommate’s pliant body, wanting to savor for just a moment what it might feel like if this were real before it all gets washed away. 

Almost out of time, he reaches for the blindfold not caring it’s against the rules. Dean’s not sure how Cas knew what he was doing but his friend’s hand grabs his wrist, keeps him from yanking the cloth free. “No,” Cas says in a voice that sounds strained, maybe fearful. “Not yet.”

And Dean relaxes, his face pressing into the space against Cas’ neck where it seems to fit so well. 

Maybe if he closes his eyes he can hold onto this dream.


	40. Time 40: Harry Potter Marathon

Time 40

“I still can’t believe you never saw these,” Gabriel comments around a mouthful of popcorn. “I mean Sam is such an uber nerd I thought for sure you had lost your virginity way before now.”

“Do not ever talk about my non-existent virginity and my brother in the same sentence again,” Dean grumbles. But instead of pulling away he lounges further across the couch and plops his head into Gabriel’s lap. 

Gabriel grins without looking away from the television, picking up some more popcorn with one hand while his other moves to splay across Dean’s t-shirt covered chest. This is new for them, this cuddling. Gabriel likes it, hopes for a lot more of it, never wants it to end. 

“Which movie is this?” Dean asks sounding a little confused. 

“The Prisoner of Azkaban,” Gabriel huffs. It would help if Dean would quit dropping off to sleep in the middle of the movies. “We have a long way to go.”

Dean grumbles noncommittally and Gabriel scratches at his chest a little before rubbing distractedly up and down Dean’s chest as he loses himself in the film. He’s seen it a hundred times, it’s one of those things he enjoys doing because he would never have been allowed to watch them at home. Not with the level of religion his parents practice. Even more so, he certainly wouldn’t have been allowed to watch anything with Dean’s head pillowed in his lap. 

But Gabriel’s grown now, has his own life, and if he wants to spend his weekend in his pajamas watching movies about wizards and muggles with his boyfriend snuggled up to him he can do it and the world can kiss his ass. 

Dean’s soft snore draws Gabriel out of his thoughts and suddenly the line of skin bared across Dean’s stomach from where his t-shirt is riding up is way more interesting than the movie. Gabriel stretches his hand out and drags the t-shirt up a little further so he can slide his hand across his boyfriend’s warm belly. Dean shifts under his hands, grumbling in his sleep and pressing closer. Gabriel smiles, bends down and presses a kiss to where Dean’s forehead meets his hairline. He loves this guy, really loves him. 

Wants to spend forever with him. 

Under the shirt is great, under the loose fitting pajama pants would be better. Dean hips lift up slightly as Gabriel’s fingers trail under the elastic. He can’t reach any further effectively so he contents himself with gentle touches through the trail of hair Dean has there. Gabriel’s hard, he bites his lower lip tasting butter and salt and Dean. 

This isn’t the first time they’ve gotten distracted. It’s honestly no wonder Dean’s a little tired. But Gabriel’s thinking he could go again and as far as he knows Dean’s never turned down sex. 

“Pause the movie.” Dean’s voice is gruff from the few moments of sleep he’s gotten and it sends a spike of want through Gabriel pooling in his groin. He fumbles for the remote but manages to comply with Dean’s order. 

They tumble together on the couch, not finished until long after the screen’s gone black. 

A year later, whenever someone mentions Harry Potter, Dean will yawn and Gabriel will blush. They’ll both immediately get erections.


	41. Time 41:  first time getting kinky

Time 41

“Don’t come until I say you can.”

It’s a simple order, rumbled out in that dragged over gravel voice that Dean loves so well. Dean’s good at following orders, been doing it most of his life. But there’s something about the simplicity of this one that makes his body immediately ache for release. He whines around the gag in his mouth and tugs on the rope tying him to the bed posts. 

Nothing gives but his resolve; he might be finished before they really even get started. 

Cas must be just to the side of the bed, that’s where his voice had originated from. Dean hadn’t heard footsteps so he assumes his lover is still there. But then, you know what they say about assumptions. 

His dick is grabbed at the based, fingers pressing tight as he squirms and thank god, the urge to come fades under the pressure. “Am I going to have to use the cock ring?” Cas asks like he’s discussing what kind of pie to order after dinner. 

The words “cock ring” should not make Dean want to beg for it. He’s grateful for the gag. 

He shakes his head finally, realizing when the grip doesn’t loosen that Cas is waiting for his answer. 

The hand slips away and that’s when Dean gets a little blurry on the passage of time. 

Cas starts with a massage, working the tension out of Dean’s muscles like he’s gone to school for it somewhere. It goes on for hours, or minutes, Dean’s not sure. But before it’s over Cas has coaxed his knees apart and his legs up and his tongue is dragging along the inside of Dean’s thigh just slow enough for Dean to be confused about where he’s going as he ignores his aching, leaking dick and nudges past his balls. 

The first press of that hot, wet muscle against his ass has Dean screaming behind the material blocking his mouth. It’s wonderful, it’s torture, he wants it to go on forever, he’s begging for Cas to stop. 

He doesn’t know what the hell is happening but at some point his mouth is replaced by fingers, one then two, then three. They’re rubbing his prostate until Dean feels precome pouring out of his dick in a steady stream to settle on his quivering belly. It’s not enough to make him come, it’s too much. He knows he’s crying, feels the wetness marking his face. He could safe word, Cas would stop. Dean knows it, loves him for it, the complicated series of taps his lover had made sure Dean memorized before he had agreed to this. 

It’s how much care Cas has put into everything that keeps Dean from coming or quitting. He’s not used to giving up all of his control, but for this man…anything. 

The fingers slide free just long enough for Dean to panic before Cas’ weight settles against him and the now familiar push of his length slides inside. He forces Dean to bend, knees over Cas’ shoulders as he pounds into his body. 

“Not until I say, not until I say,” growled out over and over like a prayer as he thrusts. Dean holds on, needs this, wants to give this to Cas. 

His thrusts quiver, fall off rhythm and Dean’s dying he needs to come so bad he hurts with it. “Now, Dean.” Cas barks sharply on his last almost violent thrust in. 

Dean follows that order gladly, almost before he processes it entirely. Light shines out behind the blindfold and the world drops away into blackness at the force of his orgasm. 

It’s fine, Cas will handle it. Dean can trust him.


	42. Time 42: first time naked in a bed

Time 42

“Slow down,” Cas grumbles as Sam slides his hand too roughly over his hip, across his thigh. “We finally, actually have all night.” 

Sam knows…fuck, he knows. They’ve been sneaking and dodging for six months, two weeks, three days, and nine hours trying to hide this still somewhat new facet of their relationship from Dean. Sam more because he doesn’t want the lecture about deflowering fallen angels and Cas…well Cas because he doesn’t want the lecture about deflowering little brothers. 

If Dean only knew how deflowered they were…Christ. 

“Sorry,” Sam murmurs into the damp skin of his lover’s shoulder. “Old habits, I guess. I keep waiting for him to bust in the door.” 

“He won’t,” Cas assures him. For a moment he has Sam distracted by the press of gentle kisses along his cheek, down the side of his neck. But it only takes a few moments of breathless gasping for Sam to notice how sure Cas sounds about Dean not interrupting them. 

“What did you do?” 

Cas bites his lower lip before taking a deep breath. “I told him.” 

“You. Told. Dean.” Sam whispers. The finality of it Earth shattering. “YOUTOLDDEAN!?”

“Yes,” Cas snaps, rolling them over so he’s on top and shoving Sam’s thighs apart so he press in close and rub his body against Sam’s as he answers, “I’m tired of longing looks and sneaking kisses, I’m tired of sticky jeans and aching jaws, stolen moments when I’m never sure we’re going to have another. I’m sick of sleeping alone and aching to hold your hand. I’m eternally frustrated by how much more of you I want all the time when it’s never enough. You’re mine. I’m yours. We both belong to Dean. He’ll get used to it, get over it, or join in with it. I frankly don’t care at this point. But by the time the sun rises I’m going to have opened you up, buried myself inside you, and marked you as mine. Then if we’re both really lucky you’ll get a chance to do the same for me before he shows up here two hours before he swore me he would with doughnuts and coffee.” 

“You kicked him out,” Sam says slowly, like he’s still on shaky ground about the whole concept. 

“We came to an agreement,” Cas nods. “We get a few nights alone a month and we promise to never EVER have sex in the Impala.”

“We’ve already had sex in the Impala.”

Cas grins, large and knowingly, like a cat who got the cream. “Dean doesn’t know that.” 

Sam’s still occasionally chuckling later, even as Cas opens him slowly, relentlessly. It’s not until the weight of the other man, who was once a celestial being, settles against Sam’s back that Sam closes his eyes and lets it all go as he so rarely gets the chance to do. Cas is around him, against him, inside him and even though neither of them have wings it feels like they’re flying somewhere between their tangled fingers and gasped breaths. 

By the time Dean shows up in the morning, two hours early with coffee and doughnuts in tow, Cas is limping his way to the bathroom and Sam is sprawled in the middle of the disheveled bed gleefully cataloging all the places he aches in that he’s never ached in before. 

Dean makes a gagging noise and Sam smiles. 

His life is very occasionally perfect, in incredibly unpredictable ways.


	43. Time 43:  Grace bonding

Time 43

He doesn’t really want to.

It’s sad, really. Gabriel knows this is supposed to be his great reward for actually helping out with that whole apocalypse thing. Being given permission to blend your grace with another angel is very rare, almost unheard of, a gift from Father. 

But Cas is just standing there…glaring at him like Gabriel hasn’t showered or worn deodorant in the last millennia. It’s kind of hard to get an angel erection when your pre-selected grace bonding partner is looking at you like that. 

Gabriel’s a hot commodity, damn it. Cas isn’t so bad himself, when you think about it. But Gabriel’s a little fuzzy on how the two black sheep of the family got shoved together for this thing. It wouldn’t be so bad if he legitimately didn’t care. But let’s be honest here, Gabriel wants this. He wants to belong with someone so totally that he never has to worry about them leaving or shoving him away. He wants that link between himself and another being after having been on his own for so long, after dying alone. 

After being reborn…alone. 

Gabriel never wants to be alone again. Cas looks like he would rather bond with Lucifer. 

The fuck is his luck sometimes. 

Gabriel’s so busy trying not to show how upset he is at the rejection from his bondling he almost misses the first gentle touch of Cas’ grace against his own. Gabriel flinches, jerking at the rolling, twisting confusion that Cas’ inquisitive grace brings along with it. Gabriel’s struck suddenly at Cas’ bravery. He’s clearly afraid, hurting even, old wounds that have never healed after falling not once, but twice in such a short time. But still, Cas persists, even through his own anxiety that Gabriel might not want him. How stupid is that? Who wouldn’t want the angel that fought Heaven to save the world? 

He feels Castiel’s grace prod at his armor, seeking an opening, trying to forge a link. Gabriel pulses back a welcome, it’s shaky, showing his insecurities more than he wants it to, but everything about Cas eases and the hesitant prodding of his grace transforms into being enveloped in everything that makes Cas who he is. 

It’s like falling into caramel. Gabriel surges forward, grace and body combined, and flings everything he is at Cas; gasping with joy when the other angel welcomes him without reservations. Hours, maybe days pass before Gabriel aware of more than his bond-mate. Their link fully sealed now, power, emotions, and light flowing between them as if they are one. Cas’ wings are a mess, damaged and broken in so many places Gabriel realizes now it wasn’t disgust on his face before, it was shame. He knits them back together with his grace and his fingertips, soothing and smoothing until Cas quivers in his arms. 

He’s shocked by how comfortable Cas is in his body. Most angels hate being in vessels but his new mate’s grace sings to him of the possibilities of their flesh and Gabriel relaxes with happiness. They’re more similar than they seem. He can’t wait to take Cas to bed. He’s contemplating all the possibilities when his mate suddenly shoves him down and claims his mouth in a searing kiss. Gabriel blinks up at Cas from the bed as the other angel traces his face with tender presses of his lips. 

“You’ll forgive me,” Cas rumbles and he bites into the lobe of Gabriel’s ear just hard enough to make him moan with want. “All I really understand of sex I’ve learned from the Winchesters.”

Oh, Father, bless those two stupid boys. “I actually think you might have had good teachers,” Gabriel chokes out as he grabs Cas’ wing joints and tugs until his mate groans. “Just forget everything they told you about relationships.” 

Cas hums, but Gabriel can feel his grace burst with laughter. They’re going to be just fine.


	44. Time 44: Lucifer has to get over his ew, humans thing because his current body keeps telling him oooo, Sam Winchester.

Time 44

“I don’t want this. I don’t want you.” 

Sam looks at himself through the mirror. He jerks and twists inside his own mind and feels the icy cold of Lucifer’s grace slam down against his soul that much harder. 

Sam’s not in the driver’s seat right now. He needs to remember that. He needs to survive. But as he watches his own hand, now outside of his control, trailing across his naked chest he can’t help but think back, Could have fooled me.

Lucifer gives him freezing agony for his sarcasm. If Sam had control of his mouth right now he would be temped to spit at himself. Instead, that traitorous hand brushes across his left nipple and Sam feels goose bumps breaking out all across his skin. 

Hot spot, and fuck, Lucifer probably knows every single one of them. 

But then Lucifer stops, he puts a shirt on, walks away. 

Sam spends the next six months trapped in his own mind with no one to talk to but his arch-enemy. The sad thing is that Lucifer is just as lonely, just as messed up as Sam is. In the end, it’s not so much that they beat him, more that Lucifer just decides he doesn’t really want to win. 

He just doesn’t want to be alone anymore. Honestly, neither does Sam. He’s gotten used to having someone there to talk to all the time. Lucifer’s actually a pretty good listener when he wants to be. 

Sam might actually like the guy…a little bit…wow, he’s still figuring out how fucked up he is. It’s all kinds of wrong. 

Another night, another hotel room, another bathroom mirror…this time it’s Sam driving as his hand slides across his bare chest. He feels Lucifer actively turning his icy presence into something warmer, more welcoming. It helps Sam to relax. 

He’s not sure why he agreed to this but he doesn’t stop even as his fingers flick over his nipple and a shiver runs down his spine. He feels the low hum of Lucifer’s approval, the sharp edge of the angel’s want plucking at his insides. 

Never had a body before, never felt anything like this; Lucifer’s excited, a little bit terrified. He’s trying to keep it all balled up inside but Sam can feel it pooling out faster that Lucifer can draw it back in. 

Sam wants this to be good. He’s not exactly sure why. 

His hand dips lower, Sam’s not even sure when he got hard. It’s distracting doing it this way. Sam has to keep his eyes open so Lucifer can see; he has two different urges in his hand, one to go faster, the other to go slower. Neither one of the urges belongs to him. Lucifer’s like a kid trying this for the first time. He’s got no idea what he wants and he’s sure Sam is doing it wrong. 

Sam bites his lip to keep from snapping at himself like a maniac and keeps up as steady a pace on his dick as he can with all the distractions. 

The orgasm seems to come out of nowhere. Sam feels his mouth moving and can hear his voice shouting his own name. Lucifer surges to the front in the final moment flailing in the sharp-hot shock of climax. 

Afterward, Sam curls into his bed with his arms tight around his own chest. Lucifer pressing kisses up and down Sam’s arm with his own mouth. It’s affection…in a crazy sort of way. Lucifer’s content and Sam’s not feeling too badly himself.


	45. Time 45:  First time on Earth

Time 45

His wings flap out when she kisses him. 

Or rather, they try to. He’s bound them so tightly they might never flap again. It’s a small price to pay for his freedom. 

Over a century later he will think about this first time and snort with laughter. It will be hard to imagine himself so fragile, so naive. 

Kali takes him to the edge with kisses, he has to shove backwards, lick at his lips and whimper before he spills everything, grace and all, too soon. This is new, this physical body, this pleasure that should just be housed in bone and skin but instead heats his grace to burning, turns his wings to fire within their bonds. 

In this moment, Gabriel can think of nothing better than her dark hands tracing the lines of his body, her hot mouth as it trails across his chest as he pants, gasps, pleads for something. He’s not sure what he needs. 

He hates not knowing things. 

She teaches him, slowly, almost painfully, over the course of one of the longest, most frustrating, most pleasurable nights of his very long existence. She drags his mouth to where she wants it, holds him there until he learns the motions she wants him to master. He’s always been a quick study. Then she shoves him back, full of command and mastery and shows him what this self-made body he feels so trapped in can actually do, can really feel. 

It’s like flying into the sun, it’s like being reborn into something new, something exposed but powerful. Kali wields her sexuality like Gabriel once handled his sword. She’s magnificent. 

When the dawn breaks Gabriel is raw, shaken to the core of his being, and abandoned. The world has changed, he has changed, his purity, his last connection to his home, now severed. 

He closes his eyes and weeps for all that he has given up, for all of the pieces of himself that he has broken. It will be the last time he cries in over a thousand years. 

By noon, Gabriel has gathered himself and follows the trail Kali has left behind her. It’s faint, maybe she doesn’t want to be found, but what he had with her last night is more of a connection than he has shared with any living being since diving from the skies of his home. He doesn’t want to lose it, not yet. 

Gabriel’s not quite ready to be totally alone.


	46. Time 46: first time having sex with a new partner. After months of pining for his (seemingly straight) gorgeous blue-eyed roommate, Dean finally has Castiel all to himself.

Time 46

He’s been unobtainable for as long as Dean can remember. 

His roommate, Cas, is a good guy, a great friend, and unfortunately the number one obsession in Dean’s sexual fantasies for the last three years. 

Unfortunately, because Cas is straight. Or Cas just isn’t interested in Dean, which is something Dean just can’t stand to think about, so Cas is straight. 

Cas has to be straight. 

There’s just no other reason for Cas not picking up on Dean wanting him. 

So why is Cas kissing that guy over there?

The fuck. 

Dean’s turning toward the door and pushing his way out into the night away from the party before he can really think it through. In the end, he takes the car. Let Cas’ little fuck buddy give him a ride home. Dean’s to upset to care about it being a dick move to do to your best friend. 

Dean crawls into bed and yanks the covers up to his face. He slips into sleep thinking about how much he wishes he was that other guy. 

“ASS!” 

Cas’ angry growl snaps Dean awake faster than the chilled, soaking t-shirt that slaps him in the face. 

He hurls himself into a sitting position to find Cas standing at the end of his bed, shirtless, freezing, and pissed as hell. 

“You fucking ditched me!” 

Cas almost never curses. 

“You drove off, didn’t even tell me, and made me look like an idiot in front of our friends. I walked home in the rain, you son of a bitch.” 

Dean’s not sure how to respond, frozen in his bed, clenching Cas’ soaked t-shirt to his chest while he watches his roommate methodically strip out of his dripping clothing while he rants away. It’s almost like one of Dean’s favorite fantasies. 

All right, it’s exactly like one of Dean’s favorite fantasies. He likes Cas angry. 

It takes Dean a second to realize the rant has abruptly cut off mid-stream. 

“Dean?” Cas questions hesitantly. “Are you listening to me?”

Dean registers cold lips and a hot mouth, wet, tangled hair in his fist, bare skin, so much bared skin all over this man he wants to badly. He’s not sure when he got out of bed. 

He answers, but what comes out might not be coherent. It doesn’t seem to matter, Cas chuckles, pushing Dean back into his bed and crawling in after him before pulling the covers up over them both. 

“Took you long enough,” Cas whispers before doing totally filthy things to Dean’s ear. “Now warm me up you jerk.”

Dean tries for sensitive; it’s not really his thing. His hands drag up and down Cas’ body trying to replace heat against the still chilled and damp skin. 

“Not like that,” Cas growls, reaching over to the nightstand and dropping the tube of lube onto Dean’s chest. “From the inside.” 

“I love you.” Dean blurts it out as he struggles with the lube. Then he flushes pink with what he just said. 

Cas smiles a rare, relaxed grin. “I know, same here, now please could you fuck me?” 

Dean’s certainly not going to argue with that.


	47. Time 47: Jo/Anna – first time together.

I skipped this one. Unwritten prompt but I have a placeholder in case I return to it.


	48. Time 48: first time having sex where it WASN'T crazy, rushed, oh god it's the end of the world, sex.

**Time 48**

Dean keeps waiting for his phone to ring, for Sam to come bursting through the door, for an explosive flash of light, an explosion…something. 

So far, things are good. In his experience that is seriously weird. 

“Are we really going to do this?” He asks softly even as he nuzzles his nose up the side of his partner’s cheek. 

The fallen archangel looks just as confused as Dean feels. Gabriel’s got his forehead all scrunched up and his eyes keep darting all over the room like he’s expecting something horrible. “You mean have sex?” 

“I know we’re having sex,” Dean sighs. “I mean are really doing it without, like, the threat of death?”

“I didn’t think you were that kinky, Dean.”

It says a lot about Dean’s state of mind that the snark pouring out of his…boyfriend…is what finally makes him relax. “Shut up and kiss me, Feathers.” 

Gabriel smirks, but then there’s kissing. Dean loses himself in hot, wet drag of Gabriel’s tongue against his own. He’s distracted by the gentle touches when they usually only have time for frantic groping. By the time they’re naked and curled together on the bed Dean’s feeling like a virgin all over again. 

It’s been so long since he felt safe; since he felt this good. 

He wonders what it must be like for Gabriel after a millennia of hiding and running for his life. Dean thinks the answers might be hidden in the hiccupping gasps escaping his lover as Dean purposefully drags out his movements and slows down his touches. 

They have time. They finally have time to do this right. 

Gabriel’s shaking apart as Dean finally prepares him. The slick slide of Dean’s fingers leaving him trembling and whimpering against Dean’s neck. 

“I love you,” Gabriel blurts as Dean slides slowly inside. “Oh…I _love you_.” 

Dean doesn’t even try to hide his smile. Gabriel has the nerve to sound surprised. 

“I love you, too,” Dean murmurs as he finds his rhythm. He’s going so slowly he hurts. But it’s worth it to have this, to have something. 

He’s lost so much. Dean was starting to think that was all life was about…losing. But now, in this moment, he’s found something wild and quicksilver free in this man beneath him. Maybe they get more than just tonight, maybe they get forever. Dean doesn’t know. 

This chance is going to have to be enough, for both of them.


	49. Time 49:  First time bondage. Dean is willing to give up control completely.

**Time 49**

He’s bound and blindfolded. 

Let’s face it, for Dean, this is nothing new. 

Well…except the sheets are clean beneath him and the ties that bind him aren’t making his wrists bleed. So that’s an improvement. 

He sucks as a sub. 

It’s something he was worried about from the moment Gabriel mentioned it. It was one of those side comments that the ex-angel was always making. One of those things that seems like a joke until about five hours later when Gabriel’s showing you the silk he wants to tie you down with. 

Frankly, Dean’s not sure why he didn’t just yell “Hell _no!_ ”

“That’s a lie,” Gabriel murmurs as he swipes a hand down Dean’s quivering flank. “You did tell me there was no way you would do this. But here we are.” 

Maybe there’s some of that angel shit left in his head somewhere. Dean doesn’t know. 

He jerks against the bindings again. He doesn’t know how long he’s been here waiting for Gabriel to do something, to do anything. 

Dean finally huffs in frustration and collapses into the mattress feeling the knots and tension in his body built up from years of scratching and fighting to survive slip away. He shivers at the kiss Gabriel presses into the center of his back. 

“There you go,” Gabriel whispers sounding proud and in control. “Finally. I’ve got you now.” 

Dean shocks himself as the first sob leaves him breathless. He doesn’t even know when the tears started but they wrack his body. It’s so loud. He doesn’t understand how he can be crying so loudly. 

He’d been expecting a beating; something brutal and physically painful in a way he understands, can cope with. But instead Gabriel takes him under with soothing strokes and long drags of his fingernails across his back and down the insides of his thighs. 

Gabriel massages him, strokes him, at one point wraps his arms around Dean and rocks him gently as he cries himself out. When Gabriel takes him, and take Dean he does; it’s with deliberate movements designed to keep Dean from guessing his next move. He leaves Dean anchored securely by Gabriel’s body, by Gabriel’s will. 

When he’s finally allowed to orgasm he feels like he flies right out of his body. 

When Gabriel brings him back up out of the space he’s dropped himself into Dean curls into his side and sleeps like he hasn’t slept since he was child. 

The next day he spends an hour staring at himself in the bathroom mirror with a lopsided grin. He has no idea where all the marks on his body came from. 

When he finally wanders back out into the hotel room Gabriel touches every single one of those marks and smiles a secret smile that Dean can’t help but return.


	50. Time 50: Dean's first time bottoming for Castiel.

**Time 50**

“I don’t think you’re supposed to be this tight.” Cas comments in that flat, deadpan voice he uses when he’s panicked but doesn’t want anyone to know.

“How the fuck would you know!” Dean snaps before he can stop himself and then winces as Cas jerks his finger out of Dean’s ass as fast as he can. 

“Maybe we shouldn’t do this,” Cas offers as he folds back into himself like he’s done something horrible and thinks he deserves to be punished. “Things were fine the way they were. It was a bad idea.”

“Dating me was a bad idea, Cas,” Dean huffs before rolling over and reaching out to drag his boyfriend up to snuggle. “Pretty much the worst idea you ever had. But since you went ahead with it, you’re kind of stuck with me now. It’s not your fault I can’t relax.”

“I must be doing it wrong.” Cas mumbles into Dean’s neck and so help him Dean can’t stop the chuckle that bubbles up inside him. 

“You’re barely doing anything,” Dean snorts. “How could you possibly be doing it wrong?” 

“Fuck you.” Cas blurts as he tenses up in Dean’s arms. 

“That’s what we’re here for.” Dean smiles as Cas tries to shove him off the bed only to drag him back close and kiss him again. “Try again,” Dean whispers as he guides Cas’ trembling hand back around his body. “Please.” 

It’s not exactly something they write about in romance novels at first. Dean’s still tense and Cas too nervous. 

“You like this?” Dean gasps as Cas slides in a third finger, so slick, he feels so stretched. 

“I love this,” Cas gasps out. He sounds stunned and overwhelmed. It sounds like he’s drowning. Dean looks over his shoulder and sees Cas’ gaze fixated on where his fingers are diligently working his way into Dean’s still somewhat resistant body. 

And yeah, that’s really all kinds of hot.

Something changes, the air’s charged and Dean’s slow to respond body suddenly eases, Cas’ fingers slide deeper and brush over something that makes Dean shake and moan. 

Cas moans with him, deep and rough, like he does when Dean’s deep inside him and gripping him tight. 

“Okay,” Dean gasps out, “enough of the previews. Move this onto the main event.” 

He’s a little shocked when Cas doesn’t comment. But then there’s scrambling behind where he’s kneeling and Cas is all but licking his way up Dean’s spine before lining himself up with shaking fingers and whimpering as he pushes slowly inside. 

Dean exhales, biting his lip as the strange feeling of being filled for the first time. It’s not bad, it’s not really fantastic either. But Dean can feel Cas gripping his hips, can hear his panting breaths as he tries to hold himself together. 

It’s good. It’s powerful. It’s them and because it’s the two of them together it’s wonderful. 

Cas’ control snaps and Dean loses himself in the way this person he loves feels as he comes inside Dean’s body. He’s doesn’t come, not that first time. It doesn’t matter. 

Cas finishes him off with a hell of a blow job.


End file.
